Benzoyl chloride → 1-Methyl-2-phenyl-1H-thieno(3,2-d)pyrimidine-4-one

HRID 557142Notes

Reaction equation

HRID 557142 reaction equation
[CH3:1][NH:2][C:3]1[CH:7]=[CH:6][S:5][C:4]=1[C:8]([NH2:10])=[O:9].[C:11](Cl)(=O)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>ClC(Cl)Cl>[CH3:1][N:2]1[C:3]2[CH:7]=[CH:6][S:5][C:4]=2[C:8](=[O:9])[N:10]=[C:11]1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 7412Benzoyl chlorideHCID 183589933-Methylamino-thiophene-2-carboxylic acid amide

Product 1

HCID 669912441-Methyl-2-phenyl-1H-thieno(3,2-d)pyrimidine-4-one

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

1.70 g (10.9 mmol) 3-Methylamino-thiophene-2-carboxylic acid amide were dissolved in 20 ml trichloromethane and 3.82 g (3.16 ml, 22.2 mmol) benzoyl chloride were added. The mixture was boiled for 90 min. After filtration the residue was dissolved in trichloromethane and washed with saturated sodium bicarbonate solution. The organic solution was dried over magnesium sulfate and evaporated under vacuum. The crude product was purified by column chromatography on silica, eluent dichloromethane/methanol 95/5.

Workup

  1. filtrationAfter filtration the residue
  2. dissolutionwas dissolved in trichloromethane
  3. washwashed with saturated sodium bicarbonate solution
  4. dry with materialThe organic solution was dried over magnesium sulfate
  5. customevaporated under vacuum
  6. customThe crude product was purified by column chromatography on silica, eluent dichloromethane/methanol 95/5

Sources & evidence

ORD record
ord-33105babf7fa435ebf8884d8a2d3d89f
Source dataset
uspto-grants-2011_11
Patent number
US08058431B2

Reaction notes

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