3,4-dihydro-2H-pyran → 4-(5-iodo-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazol-4-yl)-2-(methylthio)pyrimidine

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Reaction Conditions

Reaction Steps

A mixture of compound A (75.0 g, 0.235 mmol), DHP (39.6 g, 0.471 mmol) and TsOH.H2O (7.5 g) was stirred at 60° C. for 6 h. The mixture was cooled to room temperature and concentrated. The residue was purified by chromatography (EtOAc:petroleum ether=1:15) to give 4-(5-iodo-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazol-4-yl)-2-(methylthio)pyrimidine (B) (57.6 g, 60.8%). 1H NMR (400 MHz, CDCl3): δ 8.495 (d, 1H), 8.400 (s, 1H), 7.638 (d, 1H), 5.398 (m, 1H), 4.070 (m, 1H), 3.732 (m, 1H), 2.796 (s, 3H), 2.110 (m, 3H), 1.900 (m, 3H).

Provenance & Evidence