S-Benzylthiuronium chloride → [2-Benzylsulfanyl-6-(4-trifluoromethyl-phenyl)-pyrimidin-4-ylmethyl]-carbamic acid tert-butyl ester

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Reaction Steps

To a solution of [4-oxo-4-(4-trifluoromethyl-phenyl)but-2-ynyl]-carbamic acid tert-butyl ester (3.0 g, 9.17 mmol) and 2-benzyl-2-thiopseudo-urea hydrochloride (2.1 g, 10.1 mmol) in freshly distilled CH3CN (100 mL) was added K2CO3 (1.9 g, 13.8 mmol) at rt. After 12 h the resulting mixture was partitioned between H2O (75 mL) and DCM (50 mL). The layers were separated and the aqueous layer was extracted with DCM (2×50 mL). The combined organic layers were dried over Na2SO4, filtered and concentrated. The resulting solid was used without purification. MS (ESI): mass calcd. for C24H24F3N3O2S, 475.2; m/z found, 476.3 [M+H]+. 1H NMR (CDCl3) δ 8.15 (d, J=8.14 Hz, 2H), 7.75 (d, J=8.28 Hz, 2H), 7.51-7.47 (m, 2H), 7.39-7.31 (m, 4H), 5.52 (s, 1H), 4.51 (s, 2H), 4.43 (d, J=5.48 Hz, 2H), 1.51 (s, 9H).

Provenance & Evidence