4,6-Dichloro-5-pyrimidinecarbaldehyde → HCID 86677188, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of (2-bromo-3,5,6-trifluoro-4-pyridyl)-tert-butyl-dimethyl-silane (2.5 g, 7.66 mmol) in THF (15 mL) cooled at −78° C. was added butyllithium (2.5M in hexanes) (3.22 mL of 2.5 M, 8.05 mmol) at a rate which maintained the temperature below −70° C. On complete addition, the reaction mixture was stirred at −78° C. for 40 minutes and then a solution of 4,6-dichloropyrimidine-5-carbaldehyde (1.43 g, 8.05 mmol) in THF (25 mL) was added at a rate which maintained the temperature below −70° C. The reaction mixture was stirred at −78° C. for 1.5 hours. After this time, the reaction mixture was quenched with water and extracted with EtOAc (3×). The organics were combined, washed with water, brine, dried (MgSO4), filtered and concentrated in vacuo. The crude mixture was purified by column chromatography (ISCO Companion™, 80 g column, eluting with 0-5% EtOAc/petroleum ether) to give the sub title compound as a cream solid (1.21 g, 37.2% Yield). H1 NMR (400 MHz, DMSO) δ 8.91 (1H, s), 6.69 (1H, s), 6.48 (1H, s), 0.88 (9H, s) and 0.39 (6H, s).

Provenance & Evidence