Methanol → 4-{[3-(Methylcarbamoyl)phenyl]amino}-2-(methylsulfinyl)-6-oxo-1,6-dihydropyrimidine-5-carboxamide

HRID 869235Notes

Reaction equation

HRID 869235 reaction equation
[CH3:1][NH:2][C:3]([C:5]1[CH:6]=[C:7]([NH:11][C:12]2[N:13]=[C:14]([S:22][CH3:23])[NH:15][C:16](=[O:21])[C:17]=2[C:18]([NH2:20])=[O:19])[CH:8]=[CH:9][CH:10]=1)=[O:4].ClCCl.CO.[OH:29]OS([O-])=O.[K+]>O.C(Cl)(Cl)Cl>[CH3:1][NH:2][C:3]([C:5]1[CH:6]=[C:7]([NH:11][C:12]2[N:13]=[C:14]([S:22]([CH3:23])=[O:29])[NH:15][C:16](=[O:21])[C:17]=2[C:18]([NH2:20])=[O:19])[CH:8]=[CH:9][CH:10]=1)=[O:4]

Participants

7

Reactant 4

HCID 887MethanolHCID 6344DichloromethaneHCID 23707502Potassium hydroxy sulfiteHCID 1363757634-{[3-(Methylcarbamoyl)phenyl]amino}-2-(methylsulfanyl)-6-oxo-1,6-dihydropyrimidine-5-carboxamide

Product 1

HCID 1363757624-{[3-(Methylcarbamoyl)phenyl]amino}-2-(methylsulfinyl)-6-oxo-1,6-dihydropyrimidine-5-carboxamide

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6212ChloroformSolvent

Procedure

To a mixture of 4-{[3-(methylcarbamoyl)phenyl]amino}-2-(methylsulfanyl)-6-oxo-1,6-dihydropyrimidine-5-carboxamide (Preparation Example 306) (500 mg), dichloromethane (40 mL) and methanol (40 mL), a mixture of Oxone® (922 mg) and water (10 mL) was added and stirred at room temperature for 18 hours. To the reaction liquid, chloroform and water were added, and the precipitated solid was collected by filtration and washed with water to give 4-{[3-(methylcarbamoyl)phenyl]amino}-2-(methylsulfinyl)-6-oxo-1,6-dihydropyrimidine-5-carboxamide (234 mg) as a light yellow solid.

Workup

  1. additionwas added
  2. additionwere added
  3. filtrationthe precipitated solid was collected by filtration
  4. washwashed with water

Sources & evidence

ORD record
ord-925aa40bc840409b81f783e96a924876
Source dataset
uspto-grants-2015_03
Patent number
US08969336B2

Reaction notes

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