Water → HCID 21537752, compound

HRID 1076581Notes

Reaction equation

HRID 1076581 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:9]2[C:17]([CH3:18])=[CH:16][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][O:14][C:12]1[N:13]=[C:8]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[F:1])[C:9]2[C:17]([CH3:18])=[CH:16][S:15][C:10]=2[N:11]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 178431880HCID 178431880, compound

Product 1

HCID 21537752HCID 21537752, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 13.57 g of 4-(o-fluorophenyl)-5-methyl-1,2-dihydrothieno[2,3-d]pyrimidin-2-one in 271 ml of dimethylformamide is added 2.8 g of 63% sodium hydride. The mixture is stirred at room temperature for 1 hour. Then, 22.15 g of methyl iodide in 66 ml of dimethylformamide is added dropwise thereto. The mixture is stirred for 2 hours at room temperature. The reaction mixture is 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. From the first fraction, 2-methoxy-4-(o-fluorophenyl)-5-methyl-thieno[2,3-d]pyrimidine is obtained as crystals having a melting point of 177° - 179°C. From the second fraction, 1-methyl-4-(o-fluorophenyl)-5-methyl-1,2-dihydrotheino[2,3-d]pyrimidin-2-one is obtained as crystals having a melting point of 275° - 277°C. From the the third fraction, 3-methyl-4-(o-fluorophenyl)-5-methyl-3H-thieno[2,3-d]pyrimidin-2-one is obtained as crystals having a melting point of 176° - 178°C.

Workup

  1. stirringThe mixture is stirred for 2 hours at room temperature
  2. extractionextracted with chloroform
  3. washThe chloroform extracts are washed with water
  4. dry with materialdried over sodium sulfate
  5. customthe solvent is removed under reduced pressure
  6. customThe residue is chromatographed on silica gel

Sources & evidence

ORD record
ord-3e4ef5c0f02c48318e01e177df7d01b7
Source dataset
uspto-grants-1976_05
Patent number
US03957783

Reaction notes

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