Pyridine, hydrofluoride (1:1) → [2-(5-Phenyl-thiazol-2-ylamino)-pyridin-4-yl]-methanol

Participants

Reaction Conditions

Reaction Steps

[4-(tert-Butyl-dimethyl-silanyloxymethyl)-pyridin-2-yl]-(5-phenyl-thiazol-2-yl)-amine (8-6), 0.805 g (2.03 mmol) was dissolved in 10 mL THF and the resulting solution was cooled to 0° C. Hydrogen fluoride-pyridine (Aldrich, HF ˜70%, pyridine ˜30%) 1.20 mL was added. After 1 h the reaction was allowed to arm to RT. The THF was removed in vacuo and the residue was diluted with sat Na2CO3 (aq). The resulting precipitate was filtered to provide the pure title compound. 1H NMR (DMSO-d6): δ 11.35 (bs, 1H), 8.25 (d, 1H, J=5.2 Hz), 7.79 (s, 1H), 7.59 (d, 2H, J=7.4 Hz), 7.39 (t, 2H, J=7.6 Hz), 7.25 (t, 1H, J=7.3 Hz), 7.08 (s, 1H), 6.86 (d, 1H, J=5.2 Hz), 5.42 (bs, 1H), 4.51 (s, 2H). Mp 236-237° C. M+1: 284.0.

Provenance & Evidence