Water → HCID 21487715, compound

HRID 1076573Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:9]2[CH:17]=[C:16]([CH3:18])[S:15][C:10]=2[NH:11][C:12](=[O:14])[N:13]=1.[H-].[Na+].[CH3:21]I.O>CN(C)C=O>[CH3:21][N:11]1[C:10]2[S:15][C:16]([CH3:18])=[CH:17][C:9]=2[C:8]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[F:1])=[N:13][C:12]1=[O:14]

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of 12.4 g of 4-(o-fluorophenyl)-6-methyl-1,2-dihydrothieno[2,3-d]pyrimidin-2-one in 248 ml of dimethylformamide is added 2.58 g of 67% sodium hydride. After stirring at 50°C for 1 hour and cooling to room temperature, 20.45 g of methyl iodide in 61.4 ml of dimethylformamide is added dropwise thereto. The mixture is stirred at room temperature for 1 hour, then poured into water and extracted with chloroform. The chloroform extracts are washed with water, dried over sodium sulfate, and the solvent is removed under reduced pressure. The residue is chromatographed on silica gel using chloroform as an eluent to give 1-methyl-4-(o-fluorophenyl)-6-methyl-1,2-dihydrothieno[2,3-d]pyrimidin-2-one as crystals having a melting point of 119° - 121°C (after recrystallization from chloroform-ethanol), and 3-methyl-4-(o-fluorophenyl)-6-methyl-3H-thieno[2,3-d]pyrimidin-2-one as crystals having a melting point of 239° - 241°C.

Workup

temperaturecooling to room temperature
stirringThe mixture is stirred at room temperature for 1 hour
extractionextracted with chloroform
washThe chloroform extracts are washed with water
dry with materialdried over sodium sulfate
customthe solvent is removed under reduced pressure
customThe residue is chromatographed on silica gel

Sources & evidence

ORD record: ord-9ba8449896bd47b197f3e6fc6c49666f
Source dataset: uspto-grants-1976_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US03957783

Reaction notes

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