Trifluoroacetic acid → (3-{[2-(Morpholin-4-yl)pyrimidin-5-yl]methyl}phenyl)methanol

HRID 1021243Notes

Reaction equation

HRID 1021243 reaction equation
[Si]([O:8][CH2:9][C:10]1[CH:11]=[C:12]([CH:16]([C:18]2[CH:19]=[N:20][C:21]([N:24]3[CH2:29][CH2:28][O:27][CH2:26][CH2:25]3)=[N:22][CH:23]=2)O)[CH:13]=[CH:14][CH:15]=1)(C(C)(C)C)(C)C.C([SiH](CC)CC)C.C(O)(C(F)(F)F)=O>>[N:24]1([C:21]2[N:20]=[CH:19][C:18]([CH2:16][C:12]3[CH:11]=[C:10]([CH2:9][OH:8])[CH:15]=[CH:14][CH:13]=3)=[CH:23][N:22]=2)[CH2:29][CH2:28][O:27][CH2:26][CH2:25]1

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 86686212[3-({[tert-Butyl(dimethyl)silyl]oxy}methyl)phenyl][2-(morpholin-4-yl)pyrimidin-5-yl]methanol

Product 1

HCID 68309832(3-{[2-(Morpholin-4-yl)pyrimidin-5-yl]methyl}phenyl)methanolYield 14.2%

Procedure

[3-({[tert-Butyl(dimethyl)silyl]oxy}methyl)phenyl][2-(morpholin-4-yl)pyrimidin-5-yl]methanol (400 mg), triethylsilane (364 mg), and TFA (4 ml) were mixed, followed by stirring at room temperature overnight. The reaction mixture was concentrated under reduced pressure, and EtOAc and water were added to the obtained residue. The organic layer was dried over MgSO4 and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain (3-{[2-(morpholin-4-yl)pyrimidin-5-yl]methyl}phenyl)methanol (39 mg).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure, and EtOAc and water
  2. additionwere added to the obtained residue
  3. dry with materialThe organic layer was dried over MgSO4
  4. concentrationconcentrated under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-546a86440f9049449d5cb9e420b04e41
Source dataset
uspto-grants-2014_05
Patent number
US08716470B2

Reaction notes

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