Water → HCID 21537768, compound

HRID 1076583Notes

Reaction equation

HRID 1076583 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]3[CH2:18][CH2:19][CH2:20][CH2:21][C:16]=3[S:15][C:10]=2[NH:11][C:12](=[O:14])[N:13]=1.[H-].[Na+].[CH3:24]I.O>CN(C)C=O>[CH3:24][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]3[CH2:18][CH2:19][CH2:20][CH2:21][C:16]=3[S:15][C:10]=2[N:11]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 178517450HCID 178517450, compound

Product 1

HCID 21537768HCID 21537768, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 16.1 g of 4-(o-fluorophenyl)-1,2,5,6,7,8-hexahydrobenzothieno[2,3-d]pyrimidin-2-one in 322 of dimethylformamide is added 2.88 g of 67% sodium hydride. The mixture is stirred for 1 hour at room temperature, and 22.83 g of methyl iodide in 68 ml of dimethylformamide is added thereto at 10°C. The resulting reaction mixture is stirred for 2 hours at room temperature, 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. From the first fraction 2-methoxy-4-(o-fluorophenyl)-5,6,7,8-tetrahydrobenzothieno[2,3-d]pyrimidine is obtained as crystals having a melting point of 98° - 100°C. From the second fraction, 1-methyl-4-(o-fluorophenyl)-1,2,5,6,7,8-hexahydrobenzothieno[2,3-d]pyrimidin-2-one is obtained as crystals having a melting point of 221° - 222.5°C.

Workup

  1. customat 10°C
  2. customThe resulting reaction mixture
  3. stirringis 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-5160c9a22f64484a91a6ff7c0f56e7db
Source dataset
uspto-grants-1976_05
Patent number
US03957783

Reaction notes

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