Triethylamine → 4-Chloro-1H-pyrazolo[3,4-d]pyrimidine

Participants

Reaction Steps

Hydrazine hydrate (11.5 mL, 23.7 mmol) was slowly added to a solution of 4,6-dichloro-pyrimidine-5-carbaldehyde (40.0 g, 22.6 mmol) and triethylamine (30 mL, 22 mmol) in 1,4-dioxane (600 mL) with cooling to maintain an internal temperature below 20° C. After the addition was completed, the reaction was warmed to rt. After 1 hr, the reaction was filtered. The solvent was removed in vacuo to afford the title intermediate (29 g, 83%) as a light yellow solid. 1H NMR (400 MHz, DMSO-d6) δ14.52 (br. s, 1H), 8.83 (s, 1H), 8.45 (s, 1H). MS m/z 155 [M+1]+.

Provenance & Evidence