4,6-Dichloropyrimidine → HCID 86598743, compound

Participants

Reaction Steps

To a stirred solution of LDA (9.85 mL, 1.5 M, 15.8 mmol) in THF (20 mL) was added dropwise a solution of 4,6-dichloropyrimidine (2.00 g, 13.4 mmol) in THF (12 mL) at −78° C. After stirring for 1.5 hours, a solution of cyclopropanecarbaldehyde (1.05 g, 15.0 mmol) in THF (10 mL) was added dropwise. The solution was stirred at −78° C. for 1 hour and then quenched by addition of water (10 mL). The reaction mixture was allowed to warm to room temperature and partitioned between EtOAc and water. The organic layer was washed with brine, dried and concentrated. The residue was purified by column chromatography (hexanes/EtOAc, 3:1) to give Cyclopropyl-(4,6-dichloro-pyrimidin-5-yl)-methanol (2.36 g, 80%) as a yellow oil. 1H NMR (CDCl3, 400 MHz) δ 8.70 (s, 1H), 4.56 (m, 1H), 2.63 (d, J=8.0 Hz, 1H), 1.70 (m, 1H), 0.76 (m, 1H), 0.55 (m, 2H).

Provenance & Evidence