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

HRID 2245256Notes

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 dimethylformamide (32 ml) and stirred 20 min at 0° C. 2-Mercapto-3-methyl-6-pyrimidin-4-yl-pyrimidin-4-one (4.40 g, 20 mmol) was added to the solution and stirred 5 min and then stirred at 70° C. for 1 hour. The reaction mixture was poured into ice water, neutralized by solid K2CO3, and extracted with ethyl acetate. The organic layer was washed with brine, dried over Na2SO4 and evaporated in vacuo. Purification of the residue by silica gel column chromatography (ethyl acetate) gave the title compound (1.20 g, 27%).

Workup

stirringstirred 5 min
stirringstirred at 70° C. for 1 hour
extractionextracted with ethyl acetate
washThe organic layer was washed with brine
dry with materialdried over Na2SO4
customevaporated in vacuo
customPurification of the residue by silica gel column chromatography (ethyl acetate)

Sources & evidence

ORD record: ord-1dac84dbad2741d7b3d4a67e25123a38
Source dataset: uspto-grants-2010_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07683069B2

Reaction notes

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