Sodium borohydride → 7-[6-(4-Methoxy-benzylamino)-pyridin-2-yl]-1-(2-methyl-pyrimidin-5-yl)-hept-1-en-3-ol

HRID 860076Notes

Reaction equation

HRID 860076 reaction equation
[CH3:1][O:2][C:3]1[CH:31]=[CH:30][C:6]([CH2:7][NH:8][C:9]2[N:14]=[C:13]([CH2:15][CH2:16][CH2:17][CH2:18][C:19](=[O:29])[CH:20]=[CH:21][C:22]3[CH:23]=[N:24][C:25]([CH3:28])=[N:26][CH:27]=3)[CH:12]=[CH:11][CH:10]=2)=[CH:5][CH:4]=1.[BH4-].[Na+]>CO>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][NH:8][C:9]2[N:14]=[C:13]([CH2:15][CH2:16][CH2:17][CH2:18][CH:19]([OH:29])[CH:20]=[CH:21][C:22]3[CH:23]=[N:24][C:25]([CH3:28])=[N:26][CH:27]=3)[CH:12]=[CH:11][CH:10]=2)=[CH:30][CH:31]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 696664127-[6-(4-Methoxy-benzylamino)-pyridin-2-yl]-1-(2-methyl-pyrimidin-5-yl)-hept-1-en-3-one

Product 1

HCID 696662517-[6-(4-Methoxy-benzylamino)-pyridin-2-yl]-1-(2-methyl-pyrimidin-5-yl)-hept-1-en-3-olYield 88.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of the enone 16-1 (2.65 g, 6.36 mmol) in MeOH (150 mL) at 0° was treated with NaBH4 (0.264 g, 6.99 mmol). The ice bath was removed and the solution was stirred at room temperature for 1 hr. The reaction was quenched with water (25 mL) and extracted with EtOAc (3×125 mL). The organics were combined, dried (Na2SO4), concentrated in vacuo, and purified on silica gel (90:5:5 CHCl3:EtOAc:MeOH) to afford 2.35 g of 16-4.

Workup

  1. customThe ice bath was removed
  2. customThe reaction was quenched with water (25 mL)
  3. extractionextracted with EtOAc (3×125 mL)
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated in vacuo
  6. custompurified on silica gel (90:5:5 CHCl3:EtOAc:MeOH)

Sources & evidence

ORD record
ord-fc277c9edfc34fa0990f4cc1741ebe67
Source dataset
uspto-grants-2006_12
Patent number
US07153862B2

Reaction notes

Loading…