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

HRID 1355447
Notes
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Reaction equation

HRID 1355447 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 64774Pyridine, hydrofluoride (1:1)HCID 131723945[4-(tert-Butyl-dimethyl-silanyloxymethyl)-pyridin-2-yl]-(5-phenyl-thiazol-2-yl)-amine

Product 1

HCID 11150268[2-(5-Phenyl-thiazol-2-ylamino)-pyridin-4-yl]-methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

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

  1. customto arm to RT
  2. customThe THF was removed in vacuo
  3. additionthe residue was diluted with sat Na2CO3 (aq)
  4. 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

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes