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

HRID 1355447Notes

Reaction equation

C([SiH2][O:6][C:7](C)(C)[C:8]1[CH:13]=[CH:12][N:11]=[C:10]([NH:14][C:15]2[S:16][C:17]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[CH:18][N:19]=2)[CH:9]=1)(C)(C)C.N1C=CC=CC=1.F>C1COCC1>[C:20]1([C:17]2[S:16][C:15]([NH:14][C:10]3[CH:9]=[C:8]([CH2:7][OH:6])[CH:13]=[CH:12][N:11]=3)=[N:19][CH:18]=2)[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

Conditions

Temperature: 0 °C

Procedure

[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): δ11.35 (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.

Workup

customto arm to RT
customThe THF was removed in vacuo
additionthe residue was diluted with sat Na2CO3 (aq)
filtrationThe resulting precipitate was filtered

Sources & evidence

ORD record: ord-33de6e2d56d94b188a8a9034a80021ea
Source dataset: uspto-grants-2003_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06586423B2

Reaction notes

Loading…