Hydrochloric Acid → 2-[4-(tert-Butyl-dimethyl-silanyloxymethyl)-5-methyl-pyridin-2-ylamino]-thiazole-5-carbonitrile

HRID 1813996Notes

Reaction equation

HRID 1813996 reaction equation
[H-].[Na+].[C:3]([SiH2:7][O:8][C:9]([CH3:19])([CH3:18])[C:10]1[C:15]([CH3:16])=[CH:14][N:13]=[C:12]([NH2:17])[CH:11]=1)([CH3:6])([CH3:5])[CH3:4].Cl[C:21]1[S:22][C:23]([C:26]#[N:27])=[CH:24][N:25]=1.Cl>O.C1COCC1>[C:3]([SiH2:7][O:8][C:9]([CH3:19])([CH3:18])[C:10]1[C:15]([CH3:16])=[CH:14][N:13]=[C:12]([NH:17][C:21]2[S:22][C:23]([C:26]#[N:27])=[CH:24][N:25]=2)[CH:11]=1)([CH3:6])([CH3:5])[CH3:4]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 14852222-Chlorothiazole-5-carbonitrileHCID 1317248124-(Tert-butyl-dimethyl-silanyloxymethyl)-5-methyl-pyridin-2-ylamine

Product 1

HCID 1317248142-[4-(tert-Butyl-dimethyl-silanyloxymethyl)-5-methyl-pyridin-2-ylamino]-thiazole-5-carbonitrile

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

An oven dried flask under N2 was charged with NaH (60% dispersion, 185 mg, 4.63 mmol). 5 mL of anhydrous THF was added followed by addition of 4-(tert-butyl-dimethyl-silanyloxymethyl)-5-methyl-pyridin-2-ylamine (9-6, 0.487 g, 1.93 mmol) and 2-chloro-5-cyanothiazole (1-2, 0.391 g, 2.70 mmol). The resulting solution was heated to reflux. After 1 hour the reaction was allowed to cool to room temperature and was then diluted with water. The pH was adjusted to 7 with 1 M HCl. The resulting precipitate was filtered and washed with water to afford 9-7.

Workup

  1. customAn oven dried flask under N2
  2. temperatureThe resulting solution was heated to reflux
  3. filtrationThe resulting precipitate was filtered
  4. washwashed with water
  5. customto afford 9-7

Sources & evidence

ORD record
ord-60de5ffa22ad45769bff35b47940b766
Source dataset
uspto-grants-2005_04
Patent number
US06875767B2

Reaction notes

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