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

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Reaction Conditions

Reaction Steps

A solution of 7-bromo-6-(2-fluorophenyl)-5H-pyrrolo[3,2-d]pyrimidine (152 mg, 0.52 mmol) and methanesulfonic acid 5-(4-methoxy-2-trifluoromethylphenyl)-[1,3,4]thiadiazol-2-ylmethyl ester (211 mg, 0.57 mmol) were stirred in 2 mL DMF at 65° C. for 14 h. The solution was then heated to 85° C. for 4 h and cooled to rt. The resulting solution was filtered and purified by HPLC (10-70% MeCN/H2O with 1% formic acid). Lyophilization of the pure fractions gave 103 mg (0.183 mmol, 35% yield) of the titled compound. 1H NMR (DMSO-d6): 9.15 (s, 1H), 8.96 (s, 1H), 7.72 (d, 1H), 7.64 (t, 1H), 7.55 (q, 1H), 7.43 (s, 1H), 7.32-7.42 (m, 3H), 6.23 (s, 2H), 3.92 (s, 3H). LC-MS calculated for C23H14BrF4N5OS 563.00, found 564.35 [M+H]+.

Provenance & Evidence