Pyridine, hydrofluoride (1:1) → 2-{[6-Ethyl-4-(hydroxymethyl)pyridin-2-yl]amino}-1,3-thiazole-5-carbonitrile

HRID 1814012Notes

Reaction equation

HRID 1814012 reaction equation
[Si]([O:8][CH2:9][C:10]1[CH:15]=[C:14]([CH2:16][CH3:17])[N:13]=[C:12]([NH:18][C:19]2[S:20][C:21]([C:24]#[N:25])=[CH:22][N:23]=2)[CH:11]=1)(C(C)(C)C)(C)C.N1C=CC=CC=1.F>C1COCC1>[CH2:16]([C:14]1[N:13]=[C:12]([NH:18][C:19]2[S:20][C:21]([C:24]#[N:25])=[CH:22][N:23]=2)[CH:11]=[C:10]([CH2:9][OH:8])[CH:15]=1)[CH3:17]

Participants

4

Reactant 2

HCID 64774Pyridine, hydrofluoride (1:1)2×HCID 865882682-{[4-({[Tert-butyl(dimethyl)silyl]oxy}methyl)-6-ethylpyridin-2-yl]amino}-1,3-thiazole-5-carbonitrile

Product 1

HCID 225043012-{[6-Ethyl-4-(hydroxymethyl)pyridin-2-yl]amino}-1,3-thiazole-5-carbonitrile

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-{[4-({[tert-Butyl(dimethyl)silyl]oxy}methyl)-6-ethylpyridin-2-yl]amino}-1,3-thiazole-5-carbonitrile (12-2) (0.225 g, 0.60 mmol) was dissolved in 2 mL THF. Hydrogen fluoride-pyridine (Aldrich, HF ˜70%, pyridine ˜30%) (0.060 mL) was added. After 1.5 hours, additional hydrogen fluoride-pyridine (0.50 mL) was added. After 2.5 hours the reaction was concentrated to remove THF and the residue was diluted with 1M aqueous K2CO3. The resulting precipitate was filtered and washed with water to afford the desired compound 12-3 as a yellow solid. 1H NMR (DMSO-d6) δ 12.19 (s, 1H), 8.26 (s, 1H), 6.96 (s, 1H), 6.86 (s, 1H), 4.51 (bs, 2H), 2.79 (q, 2H, J=7.63 Hz), 1.32 (t, 3H, J=7.63 Hz). [M+H]+=261.0816.

Workup

  1. concentrationAfter 2.5 hours the reaction was concentrated
  2. customto remove THF
  3. additionthe residue was diluted with 1M aqueous K2CO3
  4. filtrationThe resulting precipitate was filtered
  5. washwashed with water

Sources & evidence

ORD record
ord-94f2a45adda14d90a89b09dfa167f2a5
Source dataset
uspto-grants-2005_04
Patent number
US06875767B2

Reaction notes

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