Dimethylformamide → 2-Methyl-4-morpholin-4-yl-thieno[3,2-d]pyrimidine-6-carboxylic acid (2-methoxy-ethyl)-amide

Participants

Reaction Steps

To 2-Chloro-4-morpholin-4-yl-thieno[3,2-d]pyrimidine-6-carbaldehyde 10 in dichloromethane (2 ml) was added 2M oxalyl chloride solution in dichloromethane (0.75 ml) followed by 2 microdrops of dimethylformamide. The reaction mixture was stirred at room temperature overnight. The solvent was removed in vacuo to give a crude product. This crude product was stirred in dichloromethane (5 ml) and to it was added 2-methoxyethylamine (34.8 μL) and triethylamine (61.5 μL). The reaction mixture was stirred at room temperature overnight. It was then partitioned between dichloromethane and saturated sodium bicarbonate solution, the combined organics were dried (MgSO4) and the solvents removed in vacuo to give a crude residue. This was purified by flash chromatography to yield 2-Methyl-4-morpholin-4-yl-thieno[3,2-d]pyrimidine-6-carboxylic acid (2-methoxy-ethyl)-amide (30 mg).

Provenance & Evidence