Sodium hydride → 6-(2-fluorophenyl)-3-[5-(4-methoxy-2-trifluoromethylphenyl)-[1,3,4]thiadiazol-2-ylmethyl]-3H-pyrrolo[3,2-d]pyrimidine-7-carbonitrile

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Reaction Steps

To a solution of 6-(2-fluorophenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carbonitrile (29 mg) and methanesulfonic acid 5-(4-methoxy-2-trifluoromethylphenyl)-[1,3,4]thiadiazol-2-ylmethyl ester (49 mg) in DMF was added NaH (5 mg). The reaction was stirred for 14 h at rt. The reaction was quenched by slow addition of AcOH (glacial), filtered, and purified by HPLC (10-70% MeCN/H2O with 1% formic acid) then lyophilized to give 5.3 mg of the titled compound (8%). 1H NMR (DMSO-d6): 9.40 (s, 1 h), 9.18 (s, 1 h), 7.85 (t, 1 h), 7.73 (d, 1H), 7.56-7.64 (m, 1H), 7.35-7.47 (m, 4H), 6.30 (s, 2H), 3.93 (s, 3H). LC-MS calculated for C24H14F4N6OS 510.5, found 511.00 [M+H]+.

Provenance & Evidence