Sodium Carbonate → 2-(4-Cyanophenyl)-5-bromopyrimidine

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Reaction Steps

--Quantities: 5-bromo-2-iodopyrimidine 2 (2.50 g, 8.77 mmol), 4-cyanophenylboronic acid 13 (1.42 g, 9.65 mmol), tetrakis(triphenylphosphine)palladium (304 mg, 0.26 mmol), DME (50 ml), aqueous 2M sodium carbonate (50 ml). The experimental procedure was as described for compound 4 to yield the cyanophenylpyrimidine 14 (1.85 g, 81%) (from MeOH), m.p. 222° C.; νmax /cm-1 (KBr) 2200 (CN), 1520, 1420s, 1120, 1015, 860 and 790; δ7.76 (2H, d, 3'- and 5'-H), 8.54 (2H, d, 2'- and 6'-H) and 8.83 (2H, s, 4- and 6-H); m/z 261 (M+), 259 (M+), 234 (M+ -HCN), 232 (M+ -HCN), 153 and 128.

Provenance & Evidence