Tetrahydrofuran → (5-Bromo-imidazo[1,2-a]pyrazin-8-yl)-(3-hydroxymethyl-4-morpholin-4-yl-phenyl)-carbamic acid tert-butyl ester

HRID 1921850Notes

Reaction equation

HRID 1921850 reaction equation
[C:1]([O:5][C:6](=[O:39])[N:7]([C:29]1[C:30]2[N:31]([CH:36]=[CH:37][N:38]=2)[C:32]([Br:35])=[CH:33][N:34]=1)[C:8]1[CH:13]=[CH:12][C:11]([N:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)=[C:10]([C:20](C)(C)[O:21][SiH2]C(C)(C)C)[CH:9]=1)([CH3:4])([CH3:3])[CH3:2].C1COCC1>[F-].C([N+](CCCC)(CCCC)CCCC)CCC>[C:1]([O:5][C:6](=[O:39])[N:7]([C:29]1[C:30]2[N:31]([CH:36]=[CH:37][N:38]=2)[C:32]([Br:35])=[CH:33][N:34]=1)[C:8]1[CH:13]=[CH:12][C:11]([N:14]2[CH2:15][CH2:16][O:17][CH2:18][CH2:19]2)=[C:10]([CH2:20][OH:21])[CH:9]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 8028TetrahydrofuranHCID 131728707(5-Bromo-imidazo[1,2-a]pyrazin-8-yl)-[3-(tert-butyl-dimethyl-silanyloxymethyl)-4-morpholin-4-yl-phenyl]-carbamic acid tert-butyl ester

Product 1

HCID 86652629(5-Bromo-imidazo[1,2-a]pyrazin-8-yl)-(3-hydroxymethyl-4-morpholin-4-yl-phenyl)-carbamic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 2724141Tetrabutylammonium FluorideSolvent

Procedure

A solution of (5-bromo-imidazo[1,2-a]pyrazin-8-yl)-[3-(tert-butyl-dimethyl-silanyloxymethyl)-4-morpholin-4-yl-phenyl]-carbamic acid tert-butyl ester (0.164 g, 0.265 mmol) in 1M tetrabutylammonium fluoride in THF (0.29 mL, 0.29 mmol) is stirred at room temperature overnight. The solvent is removed under vacuum and the residue is purified by silica gel column chromatography eluting with ethyl acetate. The title compound is isolated (0.126 g, 94%).

Workup

  1. customThe solvent is removed under vacuum
  2. customthe residue is purified by silica gel column chromatography
  3. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-8df740308284487896e1e9f775dfbdeb
Source dataset
uspto-grants-2012_05
Patent number
US08173656B2

Reaction notes

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