Water → 1-[4-(4-Fluoro-phenyl)-1-methyl-1H-pyrazol-3-yl]-1-((S)-2-{[5-(1-hydroxy-ethyl)-pyrimidin-2-ylamino]-methyl}-piperidin-1-yl)-methanone

HRID 2113538Notes

Reaction equation

HRID 2113538 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([C:14]([N:16]3[CH2:21][CH2:20][CH2:19][CH2:18][C@H:17]3[CH2:22][NH:23][C:24]3[N:29]=[CH:28][C:27]([C:30](=[O:32])[CH3:31])=[CH:26][N:25]=3)=[O:15])=[N:10][N:11]([CH3:13])[CH:12]=2)=[CH:4][CH:3]=1.[BH4-].[Na+].O>CO>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:9]([C:14]([N:16]3[CH2:21][CH2:20][CH2:19][CH2:18][C@H:17]3[CH2:22][NH:23][C:24]3[N:25]=[CH:26][C:27]([CH:30]([OH:32])[CH3:31])=[CH:28][N:29]=3)=[O:15])=[N:10][N:11]([CH3:13])[CH:12]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 670904211-{2-[((S)-1-{1-[4-(4-Fluoro-phenyl)-1-methyl-1H-pyrazol-3-yl]-methanoyl}-piperidin-2-ylmethyl)-amino]-pyrimidin-5-yl}-ethanone

Product 1

HCID 670904781-[4-(4-Fluoro-phenyl)-1-methyl-1H-pyrazol-3-yl]-1-((S)-2-{[5-(1-hydroxy-ethyl)-pyrimidin-2-ylamino]-methyl}-piperidin-1-yl)-methanone

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1-{2-[((S)-1-{1-[4-(4-Fluoro-phenyl)-1-methyl-1H-pyrazol-3-yl]-methanoyl}-piperidin-2-ylmethyl)-amino]-pyrimidin-5-yl}-ethanone (0.2 g) was dissolved in methanol 20 ml) and sodium borohydride (0.4 g) added. The reaction was stirred overnight, water was added and stirring continued for 30 min. The reaction mixture was extracted with ethyl acetate (×3), the organic extracts combined, dried (MgSO4) and solvent removed at reduced pressure to give the title compound as a colourless foam.

Workup

  1. additionadded
  2. stirringstirring
  3. waitcontinued for 30 min
  4. extractionThe reaction mixture was extracted with ethyl acetate (×3)
  5. dry with materialdried (MgSO4) and solvent
  6. customremoved at reduced pressure

Sources & evidence

ORD record
ord-840c6de275c745569bbc5b6e43e3676c
Source dataset
uspto-grants-2008_10
Patent number
US07432270B2

Reaction notes

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