Trifluoroborane-methyl sulfide → HCID 44517769, compound

HRID 2390771Notes

Reaction equation

HRID 2390771 reaction equation
[OH:1][C@@H:2]([CH3:35])[CH2:3][NH:4][C:5]1[N:10]=[C:9]([C:11]2[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=2)[N:8]=[C:7]([C:17]2[C:18]([C:25]3[CH:30]=[C:29]([CH2:31]C)[CH:28]=[C:27]([O:33]C)[CH:26]=3)=[N:19][N:20]([CH2:22][C:23]#[N:24])[CH:21]=2)[CH:6]=1.B(F)(F)F.CSC>ClCCl>[OH:1][C@@H:2]([CH3:35])[CH2:3][NH:4][C:5]1[N:10]=[C:9]([C:11]2[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=2)[N:8]=[C:7]([C:17]2[C:18]([C:25]3[CH:30]=[C:29]([CH3:31])[CH:28]=[C:27]([OH:33])[CH:26]=3)=[N:19][N:20]([CH2:22][C:23]#[N:24])[CH:21]=2)[CH:6]=1

Participants

4

Reactant 2

HCID 11137191Trifluoroborane-methyl sulfideHCID 66868286HCID 66868286, compound

Product 1

HCID 44517769HCID 44517769, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To anhydrous dichloromethane (5 mL) was added [4-[6-(2(S)-hydroxypropylamino)-2-pyridin-3-yl-pyrimidin-4-yl]-3-(3-methoxy-5-ethylphenyl)pyrazol-1-yl]acetonitrile (150 mg, 0.33 mmol) and boron trifluoride-dimethylsulfide (344 μL, 3.27 mmol) under nitrogen atmosphere. The reaction mixture was stirred for 12 hours at room temperature under nitrogen atmosphere. After completion of the demethylation, the solvent was removed by vacuum distillation, and the reaction mixture was dissolved, extracted with ethyl acetate, washed with brine, dried over anhydrous magnesium sulfate, and concentrated through vacuum distillation. Column chromatography gave the title compound (64.89 mg, 45%).

Workup

  1. customAfter completion of the demethylation, the solvent was removed by vacuum distillation
  2. dissolutionthe reaction mixture was dissolved
  3. extractionextracted with ethyl acetate
  4. washwashed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated through vacuum distillation

Sources & evidence

ORD record
ord-60b4e2b843ed46bd98e067167132db10
Source dataset
uspto-grants-2012_09
Patent number
US08273880B2

Reaction notes

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