86209-44-1 (2-氨基-4,6-双(二氟甲氧基)嘧啶,2-Amino-4,6-bis(difluoromethoxy)pyrimidine)

反应条件：

1.1 Reagents: Ammonium hydroxide Solvents: Dichloromethane , Water ; rt; 3 h, rt

参考文献：

Synthesis of 2-[[[[[4,6-bis(difluoromethoxy)-2-pyrimidinyl]amino]carbonyl]amino]sulfonyl]benzoic acid methyl ester (primisulfuron)

Wang, Jin-Ling; et al, Yingyong Huaxue, 2009, 26(4), 486-488

合成路线：1 步

100478-26-0

_95%

反应条件：

1.1 Reagents: Ammonium hydroxide Solvents: Dichloromethane , Water ; rt; 3 h, rt

参考文献：

Synthesis of 4,6-bis(difluoromethoxy)-2-aminopyridine

Wang, Jinling; et al, Nongyao, 2008, 47(5), 346-347

合成路线：1 步

100478-26-0

反应条件：

1.1 Reagents: Ammonia Solvents: Dichloromethane , Water

参考文献：

The synthesis of herbicide primisulfuron-methyl

Xiang, Dong; et al, Nongyao, 2000, 39(7),

合成路线：1 步

_39%

反应条件：

1.1 Reagents: Sodium hydroxide Solvents: 1,4-Dioxane , Water ; 70 - 80 °C
1.2 4 h, 70 - 80 °C

参考文献：

Study on the synthesis of herbicide primisulfuron-methyl for corn farmland

Lu, Yang; et al, Jingxi Yu Zhuanyong Huaxuepin, 2006, 14(15), 13-14

合成路线：1 步

_22%

反应条件：

1.1 Reagents: Sodium hydroxide Solvents: 1,4-Dioxane , Water ; 1 h, 60 - 70 °C

参考文献：

Synthesis and herbicidal activity of Primisulfuron-methyl

Huang, Mingzhi, Nongyao, 2003, 42(10), 15-16

合成路线：1 步

_18%

反应条件：

1.1 Reagents: Sodium hydroxide Solvents: 1,4-Dioxane , Water

参考文献：

Synthesis of ultrahigh effective herbicide primisulfuron-methyl

Xiao, Shenchu; et al, Huaxue Shijie, 2001, 42(7), 391-392

合成路线：1 步

1717-59-5

_18%

反应条件：

1.1 Solvents: Acetonitrile ; 3 h, 50 °C

参考文献：

Process for preparation of fluorine-containing herbicides

, China, , ,

合成路线：2 步

100478-25-9

反应条件：

1.1 Reagents: Hydrogen peroxide Solvents: Acetic acid , Water ; rt → 85 °C; 80 - 85 °C; 2 h, 80 - 85 °C
1.2 Reagents: Water
2.1 Reagents: Ammonium hydroxide Solvents: Dichloromethane , Water ; rt; 3 h, rt

参考文献：

Synthesis of 2-[[[[[4,6-bis(difluoromethoxy)-2-pyrimidinyl]amino]carbonyl]amino]sulfonyl]benzoic acid methyl ester (primisulfuron)

Wang, Jin-Ling; et al, Yingyong Huaxue, 2009, 26(4), 486-488

合成路线：2 步

100478-25-9

反应条件：

1.1 Reagents: Acetic acid , Hydrogen peroxide Solvents: Water ; rt → 85 °C; 80 - 85 °C; 2 h, 80 - 85 °C
2.1 Reagents: Ammonium hydroxide Solvents: Dichloromethane , Water ; rt; 3 h, rt

参考文献：

Synthesis of 4,6-bis(difluoromethoxy)-2-aminopyridine

Wang, Jinling; et al, Nongyao, 2008, 47(5), 346-347

合成路线：2 步

100478-25-9

反应条件：

1.1 Reagents: Hydrogen peroxide Solvents: Acetic acid , Water
2.1 Reagents: Ammonia Solvents: Dichloromethane , Water

参考文献：

The synthesis of herbicide primisulfuron-methyl

Xiang, Dong; et al, Nongyao, 2000, 39(7),

合成路线：2 步

反应条件：

1.1 Reagents: Sodium ethoxide Solvents: Toluene ; rt → reflux
1.2 reflux; 4 - 5 h, reflux
1.3 Reagents: Hydrochloric acid Solvents: Water ; neutralized
2.1 Reagents: Sodium hydroxide Solvents: 1,4-Dioxane , Water ; 70 - 80 °C
2.2 4 h, 70 - 80 °C

参考文献：

Study on the synthesis of herbicide primisulfuron-methyl for corn farmland

Lu, Yang; et al, Jingxi Yu Zhuanyong Huaxuepin, 2006, 14(15), 13-14

合成路线：2 步

反应条件：

1.1 Reagents: Sodium ethoxide Solvents: Ethanol
2.1 Reagents: Sodium hydroxide Solvents: 1,4-Dioxane , Water

参考文献：

Synthesis of ultrahigh effective herbicide primisulfuron-methyl

Xiao, Shenchu; et al, Huaxue Shijie, 2001, 42(7), 391-392

合成路线：3 步

127697-72-7

反应条件：

1.1 Catalysts: Tetrabutylammonium chloride Solvents: Acetonitrile
2.1 Reagents: Hydrogen peroxide Solvents: Acetic acid , Water
3.1 Reagents: Ammonia Solvents: Dichloromethane , Water

参考文献：

The synthesis of herbicide primisulfuron-methyl

Xiang, Dong; et al, Nongyao, 2000, 39(7),

合成路线：3 步

1979-98-2

反应条件：

1.1 Reagents: Sodium hydroxide Solvents: 1,4-Dioxane , Water ; 4 h, rt → 65 °C
1.2 Reagents: Hydrochloric acid Solvents: Water ; pH 6, rt
1.3 2 h, rt → 65 °C
2.1 Reagents: Hydrogen peroxide Solvents: Acetic acid , Water ; rt → 85 °C; 80 - 85 °C; 2 h, 80 - 85 °C
2.2 Reagents: Water
3.1 Reagents: Ammonium hydroxide Solvents: Dichloromethane , Water ; rt; 3 h, rt

参考文献：

Synthesis of 2-[[[[[4,6-bis(difluoromethoxy)-2-pyrimidinyl]amino]carbonyl]amino]sulfonyl]benzoic acid methyl ester (primisulfuron)

Wang, Jin-Ling; et al, Yingyong Huaxue, 2009, 26(4), 486-488

合成路线：3 步

1979-98-2

反应条件：

1.1 Reagents: Sodium hydroxide Solvents: 1,4-Dioxane , Water ; rt → 65 °C; 4 h, 65 °C
1.2 Reagents: Hydrochloric acid Solvents: Water ; pH 6; 2 h, 65 °C
2.1 Reagents: Acetic acid , Hydrogen peroxide Solvents: Water ; rt → 85 °C; 80 - 85 °C; 2 h, 80 - 85 °C
3.1 Reagents: Ammonium hydroxide Solvents: Dichloromethane , Water ; rt; 3 h, rt

参考文献：

Synthesis of 4,6-bis(difluoromethoxy)-2-aminopyridine

Wang, Jinling; et al, Nongyao, 2008, 47(5), 346-347

合成路线：4 步

31645-12-2

77-78-1

反应条件：

1.1 Reagents: Sodium hydroxide Solvents: Water ; rt → 10 °C; 0 - 10 °C; 4 h, 0 - 10 °C
1.2 Reagents: Hydrochloric acid Solvents: Water ; pH 2, 0 - 10 °C; 1 h, 0 - 10 °C
2.1 Reagents: Sodium hydroxide Solvents: 1,4-Dioxane , Water ; 4 h, rt → 65 °C
2.2 Reagents: Hydrochloric acid Solvents: Water ; pH 6, rt
2.3 2 h, rt → 65 °C
3.1 Reagents: Hydrogen peroxide Solvents: Acetic acid , Water ; rt → 85 °C; 80 - 85 °C; 2 h, 80 - 85 °C
3.2 Reagents: Water
4.1 Reagents: Ammonium hydroxide Solvents: Dichloromethane , Water ; rt; 3 h, rt

参考文献：

Synthesis of 2-[[[[[4,6-bis(difluoromethoxy)-2-pyrimidinyl]amino]carbonyl]amino]sulfonyl]benzoic acid methyl ester (primisulfuron)

Wang, Jin-Ling; et al, Yingyong Huaxue, 2009, 26(4), 486-488

合成路线：4 步

504-17-6

77-78-1

反应条件：

1.1 Reagents: Sodium hydroxide Solvents: Water ; rt → 10 °C
1.2 0 - 10 °C; 4 h, 0 - 10 °C
1.3 Reagents: Hydrochloric acid Solvents: Water ; pH 2, 0 - 10 °C; 1 h, 0 - 10 °C
2.1 Reagents: Sodium hydroxide Solvents: 1,4-Dioxane , Water ; rt → 65 °C; 4 h, 65 °C
2.2 Reagents: Hydrochloric acid Solvents: Water ; pH 6; 2 h, 65 °C
3.1 Reagents: Acetic acid , Hydrogen peroxide Solvents: Water ; rt → 85 °C; 80 - 85 °C; 2 h, 80 - 85 °C
4.1 Reagents: Ammonium hydroxide Solvents: Dichloromethane , Water ; rt; 3 h, rt

参考文献：

Synthesis of 4,6-bis(difluoromethoxy)-2-aminopyridine

Wang, Jinling; et al, Nongyao, 2008, 47(5), 346-347

合成路线：4 步

504-17-6

77-78-1

反应条件：

1.1 Reagents: Sodium hydroxide
2.1 Catalysts: Tetrabutylammonium chloride Solvents: Acetonitrile
3.1 Reagents: Hydrogen peroxide Solvents: Acetic acid , Water
4.1 Reagents: Ammonia Solvents: Dichloromethane , Water

参考文献：

The synthesis of herbicide primisulfuron-methyl

Xiang, Dong; et al, Nongyao, 2000, 39(7),

合成路线：5 步

105-53-3

62-56-6

反应条件：

1.1 Reagents: Sodium methoxide Solvents: Methanol , Water ; 30 min, rt; 5 h, rt → 70 °C; 70 °C → rt
2.1 Reagents: Sodium hydroxide Solvents: Water ; rt → 10 °C; 0 - 10 °C; 4 h, 0 - 10 °C
2.2 Reagents: Hydrochloric acid Solvents: Water ; pH 2, 0 - 10 °C; 1 h, 0 - 10 °C
3.1 Reagents: Sodium hydroxide Solvents: 1,4-Dioxane , Water ; 4 h, rt → 65 °C
3.2 Reagents: Hydrochloric acid Solvents: Water ; pH 6, rt
3.3 2 h, rt → 65 °C
4.1 Reagents: Hydrogen peroxide Solvents: Acetic acid , Water ; rt → 85 °C; 80 - 85 °C; 2 h, 80 - 85 °C
4.2 Reagents: Water
5.1 Reagents: Ammonium hydroxide Solvents: Dichloromethane , Water ; rt; 3 h, rt

参考文献：

Synthesis of 2-[[[[[4,6-bis(difluoromethoxy)-2-pyrimidinyl]amino]carbonyl]amino]sulfonyl]benzoic acid methyl ester (primisulfuron)

Wang, Jin-Ling; et al, Yingyong Huaxue, 2009, 26(4), 486-488

合成路线：5 步

105-53-3

62-56-6

反应条件：

1.1 Reagents: Sodium methoxide Solvents: Methanol ; 30 min, rt; rt → 70 °C; 5 h, 70 °C
2.1 Reagents: Sodium hydroxide Solvents: Water ; rt → 10 °C
2.2 0 - 10 °C; 4 h, 0 - 10 °C
2.3 Reagents: Hydrochloric acid Solvents: Water ; pH 2, 0 - 10 °C; 1 h, 0 - 10 °C
3.1 Reagents: Sodium hydroxide Solvents: 1,4-Dioxane , Water ; rt → 65 °C; 4 h, 65 °C
3.2 Reagents: Hydrochloric acid Solvents: Water ; pH 6; 2 h, 65 °C
4.1 Reagents: Acetic acid , Hydrogen peroxide Solvents: Water ; rt → 85 °C; 80 - 85 °C; 2 h, 80 - 85 °C
5.1 Reagents: Ammonium hydroxide Solvents: Dichloromethane , Water ; rt; 3 h, rt

参考文献：

Synthesis of 4,6-bis(difluoromethoxy)-2-aminopyridine

Wang, Jinling; et al, Nongyao, 2008, 47(5), 346-347

合成路线：5 步

108-59-8

62-56-6