Water → HCID 12202400, compound

HRID 1076575Notes

Reaction equation

HRID 1076575 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:9]2[CH:17]=[CH:16][S:15][C:10]=2[NH:11][C:12](=[O:14])[N:13]=1.[H-].[Na+].[CH3:20]I.O>CN(C)C=O>[CH3:20][O:14][C:12]1[N:13]=[C:8]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[Cl:1])[C:9]2[CH:17]=[CH:16][S:15][C:10]=2[N:11]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 178517447HCID 178517447, compound

Product 1

HCID 12202400HCID 12202400, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 4.0 g of 4-(o-chlorophenyl)-1,2-dihydrothieno[2,3-d]pyrimidin-2-one in 80 ml of dimethylformamide is added 0.82 g of 63% sodium hydride. The resulting mixture is stirred at room temperature for 30 minutes. Then, 6.48 g of methyl iodide in 33 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-chlorophenyl)-thieno[2,3-d]pyrimidine is obtained as crystals having a melting point of 172.5° - 174.5°C (after recrystallization from ether). From the second fraction, 1-methyl-4-(o-chlorophenyl)-1,2-dihydrothieno[2,3-d]pyrimidin-2-one is obtained as crystals having a melting point of 225° - 226°C (after recrystallization from chloroform-ethanol). From the third fraction, 3-methyl-4-(o-chlorophenyl)-3H-thieno[2,3-d]pyrimidin-2-one is obtained as crystals having a melting point of 190° - 192°C (after recrystallization from ethanol-ether).

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-1b568fce8c0b489c80eb30045252653d
Source dataset
uspto-grants-1976_05
Patent number
US03957783

Reaction notes

Loading…