Potassium Carbonate → 2-(4-Hydroxymethyl-3-methyl-pyridin-2-ylamino)-thiazole-5-carbonitrile

HRID 1814002Notes

Reaction equation

HRID 1814002 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]#[N:21])=[CH:18][N:19]=2)[C:9]=1[CH3:22])(C)(C)C.C1C=CN=CC=1.F.C([O-])([O-])=O.[K+].[K+]>C1COCC1.O>[OH:6][CH2:7][C:8]1[CH:13]=[CH:12][N:11]=[C:10]([NH:14][C:15]2[S:16][C:17]([C:20]#[N:21])=[CH:18][N:19]=2)[C:9]=1[CH3:22]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 64774Pyridine, hydrofluoride (1:1)2×HCID 1317248172-[4-(tert-Butyl-dimethyl-silanyloxymethyl)-3-methyl-pyridin-2-ylamino]-thiazole-5-carbonitrile

Product 1

HCID 113455932-(4-Hydroxymethyl-3-methyl-pyridin-2-ylamino)-thiazole-5-carbonitrile

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

2-[4-(tert-Butyl-dimethyl-silanyloxymethyl)-3-methyl-pyridin-2-ylamino]-thiazole-5-carbonitrile (10-3, 0.920 g, 2.55 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 an additional 0.5 mL of HF-pyridine was added and the reaction was allowed to stir overnight. After a total of 18 hours the reaction was diluted with water and the pH was adjusted to 7 with K2CO3 (s). The resulting precipitate was filtered and washed with water. Air drying afforded the crude product as an orange solid, which was used in the next step without further purification.

Workup

  1. stirringto stir overnight
  2. filtrationThe resulting precipitate was filtered
  3. washwashed with water
  4. customAir drying

Sources & evidence

ORD record
ord-4303301a1b054d5591b54667655d3aa6
Source dataset
uspto-grants-2005_04
Patent number
US06875767B2

Reaction notes

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