2-Amino-4-chloro-6-methylpyrimidine → HCID 13269157, compound

HRID 638478Notes

Reaction equation

HRID 638478 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]([Cl:24])[CH:21]=[C:20]([CH3:25])[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]([Cl:24])[CH:21]=[C:20]([CH3:25])[N:19]=1)=[O:15])(=[O:12])=[O:11]

Participants

4

Reactant 2

HCID 218102-Amino-4-chloro-6-methylpyrimidineHCID 110969602-Difluoromethoxybenzenesulfonylisocyanate

Product 1

HCID 13269157HCID 13269157, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
20 °C

Procedure

34.2 g of 2-difluoromethoxyphenylsulfonyl isocyanate and 19.7 g of 2-amino-4-chloro-6-methyl-pyrimidine are stirred in 40 ml of dioxane for 3 hours at 90°-100° C. The solution is then cooled to 20° C., filtered, and concentrated to about 1/4 of its volume. After addition of ether, 32.9 g of N-(2-difluoromethoxyphenylsulfonyl)-N'-(4-chloro-6-methyl-pyrimidin-2-yl)urea crystallise from the residue.

Workup

  1. filtrationfiltered
  2. concentrationconcentrated to about 1/4 of its volume
  3. additionAfter addition of ether, 32.9 g of N-(2-difluoromethoxyphenylsulfonyl)-N'-(4-chloro-6-methyl-pyrimidin-2-yl)urea
  4. customcrystallise from the residue

Sources & evidence

ORD record
ord-20037318f5414327b50e0ad003a94e55
Source dataset
uspto-grants-1985_12
Patent number
US04561878

Reaction notes

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