Potassium Carbonate → 2-(4-Hydroxymethyl-5-methyl-pyridin-2-ylamino)-thiazole-5-carbonitrile

HRID 1813997Notes

Reaction equation

HRID 1813997 reaction equation
C([SiH2][O:6][C:7](C)(C)[C:8]1[C:13]([CH3:14])=[CH:12][N:11]=[C:10]([NH:15][C:16]2[S:17][C:18]([C:21]#[N:22])=[CH:19][N:20]=2)[CH:9]=1)(C)(C)C.C1C=CN=CC=1.F.C([O-])([O-])=O.[K+].[K+]>C1COCC1.O>[OH:6][CH2:7][C:8]1[C:13]([CH3:14])=[CH:12][N:11]=[C:10]([NH:15][C:16]2[S:17][C:18]([C:21]#[N:22])=[CH:19][N:20]=2)[CH:9]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 64774Pyridine, hydrofluoride (1:1)HCID 1317248142-[4-(tert-Butyl-dimethyl-silanyloxymethyl)-5-methyl-pyridin-2-ylamino]-thiazole-5-carbonitrile

Product 1

HCID 225042912-(4-Hydroxymethyl-5-methyl-pyridin-2-ylamino)-thiazole-5-carbonitrile

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

2-[4-(tert-Butyl-dimethyl-silanyloxymethyl)-5-methyl-pyridin-2-ylamino]-thiazole-5-carbonitrile (9-7, 0.650 g, 1.80 mmol) was dissolved in 5 mL THF. HF-pyridine (Aldrich), 0.5 mL, was added and the reaction was stirred at room temperature. After 4 hours the reaction was diluted with water and the pH was adjuted to 7 with K2CO3 (s). The resulting precipitate was filtered and washed with water to afford 9-8 as an orange solid which was used in the next step without further purification. 1H NMR (DMSO-d6) δ 12.15 (s, 1H), 8.24 (s, 1H), 8.10 (s, 1H), 7.26 (s, 1H), 5.48 (bs, 1H), 4.52 (s, 2H), 2.13 (s, 3H).

Workup

  1. filtrationThe resulting precipitate was filtered
  2. washwashed with water

Sources & evidence

ORD record
ord-a9620993d8b840f7bce927c0588e0d78
Source dataset
uspto-grants-2005_04
Patent number
US06875767B2

Reaction notes

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