Hydrochloric Acid → HCID 136375767, compound

HRID 869233Notes

Reaction equation

HRID 869233 reaction equation
Cl[C:2]1[C:7]([C:8]([NH2:10])=[O:9])=[C:6]([NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([S:18]([CH3:21])(=[O:20])=[O:19])[CH:13]=2)[N:5]=[C:4]([S:22][CH3:23])[N:3]=1.C(=O)([O-])[O-:25].[K+].[K+].OO.Cl>O.CS(C)=O>[CH3:23][S:22][C:4]1[NH:3][C:2](=[O:25])[C:7]([C:8]([NH2:10])=[O:9])=[C:6]([NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([S:18]([CH3:21])(=[O:20])=[O:19])[CH:13]=2)[N:5]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 784Hydrogen PeroxideHCID 11430Potassium CarbonateHCID 86662043HCID 86662043, compound

Product 1

HCID 136375767HCID 136375767, compoundYield 75.5%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

To a mixture of 4-chloro-2-(methylsulfanyl)-6-{[3-(methylsulfonyl)phenyl]amino}pyrimidine-5-carboxamide (Preparation Example 298) (1.95 g) and DMSO (30 mL), potassium carbonate (1.81 g) and 30% hydrogen peroxide solution (2.65 mL) were added and stirred at 50° C. for 1.5 hours. The reaction liquid was ice-cooled, and 1M hydrochloric acid (25 mL) and thereafter water (150 mL) were added and stirred for 30 minutes. The precipitated solid was collected by filtration and washed with water to give 2-(methylsulfanyl)-4-{[3-(methylsulfonyl)phenyl]amino}-6-oxo-1,6-dihydropyrimidine-5-carboxamide (1.40 g) as a light yellow solid.

Workup

  1. additionwere added
  2. customThe reaction liquid
  3. temperaturecooled
  4. stirringstirred for 30 minutes
  5. filtrationThe precipitated solid was collected by filtration
  6. washwashed with water

Sources & evidence

ORD record
ord-741e276f80fd41248beec3396c2e96f7
Source dataset
uspto-grants-2015_03
Patent number
US08969336B2

Reaction notes

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