Potassium Carbonate → 2-Chloro-3-methyl-6-(pyrimidin-4-YL)pyrimidin-4-one

HRID 1784650Notes

Reaction equation

P(Cl)(Cl)([Cl:3])=O.S[C:7]1[N:12]([CH3:13])[C:11](=[O:14])[CH:10]=[C:9]([C:15]2[CH:20]=[CH:19][N:18]=[CH:17][N:16]=2)[N:8]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[Cl:3][C:7]1[N:12]([CH3:13])[C:11](=[O:14])[CH:10]=[C:9]([C:15]2[CH:20]=[CH:19][N:18]=[CH:17][N:16]=2)[N:8]=1

Participants

Conditions

Temperature: 0 °C

Procedure

Phosphorous oxychloride (4.60 g, 30 mmol) was added to dimethyl-formamide (32 ml) and stirred for 20 min at 0° C. 2-Mercapto-3-methyl-6-(4-pyrimidyl)-3H-pyrimidine-4-one (4.40 g, 20 mmol) was added to the solution and stirred 5 min and then stirred at 70° C. for 2 hours. The reaction mixture was poured into ice water, neutralized by solid potassium carbonate, and extracted with ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate, and evaporated under reduced pressure. Purification of the residue by silica gel chromatography (ethyl acetate) gave the title compound (1.20 g, 27%).

Workup

stirringstirred 5 min
stirringstirred at 70° C. for 2 hours
extractionextracted with ethyl acetate
washThe organic layer was washed with brine
dry with materialdried over sodium sulfate
customevaporated under reduced pressure
customPurification of the residue by silica gel chromatography (ethyl acetate)

Sources & evidence

ORD record: ord-ebba085ddfba44fba0632948aa1012eb
Source dataset: uspto-grants-2009_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07504411B2

Reaction notes

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