Potassium Carbonate → 2-(6-Chloro-4-hydroxymethyl-pyridin-2-ylamino)-thiazole-5-carbonitrile

Participants

Reaction Steps

2-[4-(tert-Butyl-dimethyl-silanyloxymethyl)-6-chloro-pyridin-2-ylamino]-thiazole-5-carbonitrile (11-6) was dissolved in 5 mL of THF. HF-pyr (Aldrich), 0.5 mL was added and the reaction was stirred at room temperature. After 1.5 hours the reaction was diluted with water and adjuted to pH 7 by the gradual addition of solid K2CO3. The mixture was extracted 3× with DCM. Large amounts of solid were suspended in the DCM extracts so the extracts were filtered and washed with DCM to afford the desired product, 11-7. 1H NMR (DMSO-d6) δ 12.49 (s, 1H), 8.30 (s, 1H), 7.09 (s, 1H), 7.06 (s, 1H), 5.59 (t, 1H, J=5.8 Hz), 4.55 (d, 2H, J=5.5 Hz).

Provenance & Evidence