4-(Difluoromethoxy)-6-methylpyrimidin-2-amine → N-(2-difluoromethoxyphenyl-sulfonyl)-N'-(4-difluoromethoxy-6-methylpyrimidin-2-yl)-urea

HRID 1719601Notes

Reaction equation

HRID 1719601 reaction equation
[F:1][CH:2]([F:16])[O:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10]([N:13]=[C:14]=[O:15])(=[O:12])=[O:11].[NH2:17][C:18]1[N:23]=[C:22]([O:24][CH:25]([F:27])[F:26])[CH:21]=[C:20]([CH3:28])[N:19]=1>O1CCOCC1>[F:16][CH:2]([F:1])[O:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10]([NH:13][C:14]([NH:17][C:18]1[N:23]=[C:22]([O:24][CH:25]([F:27])[F:26])[CH:21]=[C:20]([CH3:28])[N:19]=1)=[O:15])(=[O:12])=[O:11]

Participants

4

Reactant 2

HCID 28173904-(Difluoromethoxy)-6-methylpyrimidin-2-amineHCID 110969602-Difluoromethoxybenzenesulfonylisocyanate

Product 1

HCID 53792571N-(2-difluoromethoxyphenyl-sulfonyl)-N'-(4-difluoromethoxy-6-methylpyrimidin-2-yl)-ureaYield 94.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 2.5 g of 2-difluoromethoxyphenyl-sulfonylisocyanate, 1.75 g of 2-amino-4-difluoromethoxy-6-methyl-pyrimidine and 30 ml of absolute dioxane is stirred at a temperature of 70° to 75° C. for 2 hours. The solution is concentrated by evaporation, and the residue is then crystallised from ether to obtain 4.0 g of N-(2-difluoromethoxyphenyl-sulfonyl)-N'-(4-difluoromethoxy-6-methyl-pyrimidin-2-yl)-urea, m.p. 163° to 164° C.

Workup

  1. concentrationThe solution is concentrated by evaporation
  2. customthe residue is then crystallised from ether

Sources & evidence

ORD record
ord-195c49486777401b9ce4d757074abec9
Source dataset
uspto-grants-1985_09
Patent number
US04540782

Reaction notes

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