Triethylamine → HCID 89494586, compound

Participants

Reaction Steps

To a solution of 2,4-dichloro-5-methyl-5,7-dihydrothieno[3,4-d]pyrimidine 6,6-dioxide (150.0 mg, 0.5926 mmol) and Et3N (119.9 mg, 1.2 mmol) in DMF (2.0 mL) was added (S)-3-methylmorpholine (59.9 mg, 0.6 mmol) dropwise. The reaction mixture stirred overnight, then quenched by addition of H2O and the resulting mixture extracted with ethyl acetate. The organic layers were combined, washed with brine, dried over anhydrous Na2SO4, filtered and evaporated. The crude product was purified by column chromatography on silica gel (eluent: petroleum ether/ethyl acetate=20:1-2/1) to provide 4-chloro-5-methyl-2-[(3S)-3-methylmorpholin-4-yl]-5,7-dihydrothieno[3,4-d]pyrimidine 6,6-dioxide (B) as a light yellow solid (50 mg, 13.5%). Further elution then provides 2-chloro-5-methyl-4-[(3S)-3-methylmorpholin-4-yl]-5,7-dihydrothieno[3,4-d]pyrimidine 6,6-dioxide (A) as an off-white soild (100 mg, 27%),

Provenance & Evidence