Sodium borohydride → HCID 86606997, compound

HRID 1868466Notes

Reaction equation

HRID 1868466 reaction equation
[C:1]([C:4]1[N:5]=[C:6]2[N:11]=[C:10]([CH3:12])[C:9]([CH2:13][NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[C:8]([C:22]3[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][C:23]=3[Cl:29])[N:7]2[CH:30]=1)(=[O:3])[CH3:2].[BH4-].[Na+]>C1COCC1.O>[Cl:29][C:23]1[CH:24]=[C:25]([Cl:28])[CH:26]=[CH:27][C:22]=1[C:8]1[N:7]2[CH:30]=[C:4]([CH:1]([OH:3])[CH3:2])[N:5]=[C:6]2[N:11]=[C:10]([CH3:12])[C:9]=1[CH2:13][NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18]

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 86606995HCID 86606995, compound

Product 1

HCID 86606997HCID 86606997, compoundYield 110.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of tert-butyl (2-acetyl-5-(2,4-dichlorophenyl)-7-methylimidazo[1,2-a]pyrimidin-6-yl)methylcarbamate (intermediate for Example 150, 5 mg, 0.01 mmol) in THF (2 mL) and H2O (0.3 mL) at room temperature was added NaBH4 (2 mg, 0.05 mmol). After 30 min, the reaction was concentrated under reduced pressure and diluted with EtOAc. The organic layer was washed with satd aq NH4Cl and brine prior to drying over MgSO4. Filtration, concentration under reduced pressure and purification by silica gel chromatography afforded crude tert-butyl (5-(2,4-dichlorophenyl)-2-(1-hydroxyethyl)-7-methylimidazo[1,2-a]pyrimidin-6-yl)methylcarbamate (5 mg, 100% crude yield).

Workup

  1. concentrationthe reaction was concentrated under reduced pressure
  2. additiondiluted with EtOAc
  3. washThe organic layer was washed with satd aq NH4Cl and brine
  4. dry with materialto drying over MgSO4
  5. filtrationFiltration, concentration
  6. customunder reduced pressure and purification by silica gel chromatography

Sources & evidence

ORD record
ord-1dc9de9efabb46f0b3ea420d35a104e6
Source dataset
uspto-grants-2009_12
Patent number
US07635699B2

Reaction notes

Loading…