Sodium borohydride → 5-Pyrimidin-2-yl-1-({4-[5-(2,2,2-trifluoroethoxy)pyrimidin-2-yl]piperazin-1-yl}sulfonyl)pentan-2-ol

HRID 1723805Notes

Reaction equation

HRID 1723805 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[N:3][C:2]=1[CH2:7][CH2:8][CH2:9][C:10](=[O:33])[CH2:11][S:12]([N:15]1[CH2:20][CH2:19][N:18]([C:21]2[N:26]=[CH:25][C:24]([O:27][CH2:28][C:29]([F:32])([F:31])[F:30])=[CH:23][N:22]=2)[CH2:17][CH2:16]1)(=[O:14])=[O:13].[BH4-].[Na+]>C(Cl)Cl.CO>[N:1]1[CH:6]=[CH:5][CH:4]=[N:3][C:2]=1[CH2:7][CH2:8][CH2:9][CH:10]([OH:33])[CH2:11][S:12]([N:15]1[CH2:20][CH2:19][N:18]([C:21]2[N:22]=[CH:23][C:24]([O:27][CH2:28][C:29]([F:30])([F:32])[F:31])=[CH:25][N:26]=2)[CH2:17][CH2:16]1)(=[O:13])=[O:14]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 688481475-Pyrimidin-2-yl-1-({4-[5-(2,2,2-trifluoroethoxy)pyrimidin-2-yl]piperazin-1-yl}sulfonyl)pentan-2-one

Product 1

HCID 688486265-Pyrimidin-2-yl-1-({4-[5-(2,2,2-trifluoroethoxy)pyrimidin-2-yl]piperazin-1-yl}sulfonyl)pentan-2-olYield 96%

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

To a stirred solution of 5-pyrimidin-2-yl-1-({4-[5-(2,2,2-trifluoroethoxy)pyrimidin-2-yl]piperazin-1-yl}sulfonyl)pentan-2-one (9.47 g, 19.4 mmol) in DCM/MeOH (100 mL/100 mL) was added NaBH4 (807 mg, 21.3 mmol) portionwise and the reaction stirred at room temperature. The reaction was then quenched by addition of a saturated solution of NH4Cl (250 mL) and the organics removed in vacuo. The aqueous residue was then extracted with EtOAc (2×250 mL), combined organics washed with brine (250 mL), dried (MgSO4), filtered and concentrated in vacuo to give 5-pyrimidin-2-yl-1-({4-[5-(2,2,2-trifluoroethoxy)pyrimidin-2-yl]piperazin-1-yl}sulfonyl)pentan-2-ol as a white solid (9.10 g, 18.6 mmol, 96%).

Workup

  1. customThe reaction was then quenched by addition of a saturated solution of NH4Cl (250 mL)
  2. customthe organics removed in vacuo
  3. extractionThe aqueous residue was then extracted with EtOAc (2×250 mL)
  4. washcombined organics washed with brine (250 mL)
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4b4178ece7ee43d29d7ff0dcf8ee3c92
Source dataset
uspto-grants-2009_02
Patent number
US07485644B2

Reaction notes

Loading…