Water → HCID 12202392, compound

HRID 1076585Notes

Reaction equation

HRID 1076585 reaction equation
[C:1]1([C:7]2[C:8]3[CH:16]=[CH:15][S:14][C:9]=3[NH:10][C:11](=[O:13])[N:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[CH3:19]I.O>CN(C)C=O>[CH3:19][O:13][C:11]1[N:12]=[C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[C:8]2[CH:16]=[CH:15][S:14][C:9]=2[N:10]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 178517437HCID 178517437, compound

Product 1

HCID 12202392HCID 12202392, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
60 °C

Procedure

To a solution of 4.0 g of 4-phenyl-1,2-dihydrothieno[2,3-d]pyrimidin-2-one in 80 ml of dimethylformamide is added 0.8 g of 63% sodium hydride. The mixture is stirred at 60°C for 1 hour. The mixture is cooled to room temperature and 4.97 g of methyl iodide in 15 ml of dimethylformamide is added dropwise thereto at 10°C. 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-phenylthieno[2,3-d]pyrimidine is obtained as crystals having a melting point of 160° - 161.5°C (after recrystallization from ethanol). From the second fraction, 1-methyl-4-phenyl-1,2-dihydrothieno[2,3-d]pyrimidin-2-one is obtained as crystals having a melting point of 256° - 257.5°C (after recrystallization from ethanol). From the third fraction, 3-methyl-4-phenyl-3H-thieno[2,3-d]pyrimidin-2-one is obtained as crystal having a melting point of 175° - 181°C (after recrystallization from ethanol).

Workup

  1. temperatureThe mixture is cooled to room temperature
  2. customat 10°C
  3. stirringThe mixture is stirred for 2 hours at room temperature
  4. extractionextracted with chloroform
  5. washThe chloroform extracts are washed with water
  6. dry with materialdried over sodium sulfate
  7. customthe solvent is removed under reduced pressure
  8. customThe residue is chromatographed on silica gel

Sources & evidence

ORD record
ord-17a16795106441f1baa8746b5c41bd23
Source dataset
uspto-grants-1976_05
Patent number
US03957783

Reaction notes

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