Citric Acid → HCID 86662043, compound

HRID 869232Notes

Reaction equation

HRID 869232 reaction equation
[H-].[Na+].[CH3:3][S:4]([C:7]1[CH:8]=[C:9]([CH:11]=[CH:12][CH:13]=1)[NH2:10])(=[O:6])=[O:5].[Cl:14][C:15]1[C:20]([C:21]([NH2:23])=[O:22])=[C:19](Cl)[N:18]=[C:17]([S:25][CH3:26])[N:16]=1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CN(C=O)C.C(OCC)(=O)C.C1COCC1>[Cl:14][C:15]1[C:20]([C:21]([NH2:23])=[O:22])=[C:19]([NH:10][C:9]2[CH:11]=[CH:12][CH:13]=[C:7]([S:4]([CH3:3])(=[O:5])=[O:6])[CH:8]=2)[N:18]=[C:17]([S:25][CH3:26])[N:16]=1

Participants

8

Reactant 4

HCID 311Citric AcidHCID 24758Sodium hydrideHCID 4280293-(Methylsulphonyl)anilineHCID 707003774,6-Dichloro-2-(methylsulfanyl)pyrimidine-5-carboxamide

Product 1

HCID 86662043HCID 86662043, compoundYield 62.3%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolvent2×HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 55% sodium hydride in oil (733 mg) and DMF (20 mL), a mixture of 3-(methylsulfonyl)aniline (1.44 g) and THF (20 mL) were added under ice cooling and stirred for 30 minutes under ice cooling. After dropwise addition of a mixture of 4,6-dichloro-2-(methylsulfanyl)pyrimidine-5-carboxamide (2.0 g) and DMF (30 mL) over 15 minutes, the reaction liquid was further stirred under ice cooling for 15 minutes. After addition of 10% aqueous citric acid (300 mL) and extraction with ethyl acetate, the organic layer was washed with saturated aqueous sodium chloride. After drying over anhydrous magnesium sulfate, the solvent was concentrated, and the precipitated solid was collected by filtration and dried to give 4-chloro-2-(methylsulfanyl)-6-{[3-(methylsulfonyl)phenyl]amino}pyrimidine-5-carboxamide (1.95 g) as a light yellow solid.

Workup

  1. additionwere added under ice cooling
  2. customthe reaction liquid
  3. stirringwas further stirred under ice cooling for 15 minutes
  4. washthe organic layer was washed with saturated aqueous sodium chloride
  5. dry with materialAfter drying over anhydrous magnesium sulfate
  6. concentrationthe solvent was concentrated
  7. filtrationthe precipitated solid was collected by filtration
  8. customdried

Sources & evidence

ORD record
ord-c81f4eedd951401ca8ccf6676c0e4ca5
Source dataset
uspto-grants-2015_03
Patent number
US08969336B2

Reaction notes

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