Tetrabutylammonium Fluoride → (2-(5-Bromoimidazo[1,2-a]pyrazin-8-ylamino)thiazol-5-yl)methanol

HRID 1684952Notes

Reaction equation

HRID 1684952 reaction equation
[Br:1][C:2]1[N:7]2[CH:8]=[CH:9][N:10]=[C:6]2[C:5]([NH:11][C:12]2[S:13][C:14]([CH2:17][O:18][Si](C(C)(C)C)(C)C)=[CH:15][N:16]=2)=[N:4][CH:3]=1.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[Br:1][C:2]1[N:7]2[CH:8]=[CH:9][N:10]=[C:6]2[C:5]([NH:11][C:12]2[S:13][C:14]([CH2:17][OH:18])=[CH:15][N:16]=2)=[N:4][CH:3]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 57541342N-(5-bromoimidazo[1,2-a]pyrazin-8-yl)-5-((tert-butyldimethylsilyloxy)methyl)thiazol-2-amine

Product 1

HCID 57541339(2-(5-Bromoimidazo[1,2-a]pyrazin-8-ylamino)thiazol-5-yl)methanolYield 70.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The product of Step 1 (0.125 g, 0.28 mmol) is dissolved in THF (2 mL). To this solution is added TBAF solution (1M in THF, 0.31 mL, 0.31 mmol) and the reaction is stirred at room temperature overnight. The reaction is condensed and the residue purified by gradient column chromatography eluting with dichloromethane—5% methanolic ammonia (7 N) in dichloromethane to give the alcohol (64 mg, 69%). LCMS: Rt 2.54 min (97.7%). MS (MH+, m/z) 326.

Workup

  1. customcondensed
  2. customthe residue purified by gradient column chromatography
  3. washeluting with dichloromethane—5% methanolic ammonia (7 N) in dichloromethane

Sources & evidence

ORD record
ord-eae303cf81374bae9d7aebd7efdc5a5a
Source dataset
uspto-grants-2012_04
Patent number
US08148369B2

Reaction notes

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