Sodium borohydride → HCID 70656222, compound

HRID 2401309Notes

Reaction equation

HRID 2401309 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([CH:26]=[CH:27][CH:28]=1)[O:7][C:8]1[N:9]([CH2:23][CH2:24][CH3:25])[C:10](=[O:22])[C:11]2[NH:12][C:13]([CH:17]3[CH2:21][CH2:20][CH2:19][CH2:18]3)=[N:14][C:15]=2[N:16]=1)(=[O:3])[CH3:2].[BH4-].[Na+]>C(O)C>[CH:17]1([C:13]2[NH:12][C:11]3[C:10](=[O:22])[N:9]([CH2:23][CH2:24][CH3:25])[C:8]([O:7][C:6]4[CH:26]=[CH:27][CH:28]=[C:4]([CH:1]([OH:3])[CH3:2])[CH:5]=4)=[N:16][C:15]=3[N:14]=2)[CH2:21][CH2:20][CH2:19][CH2:18]1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 67192531HCID 67192531, compound

Product 1

HCID 70656222HCID 70656222, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-(3-Acetyl-phenoxy)-8-cyclopentyl-1-propyl-1,7-dihydro-purin-6-one (0.05 g, 0.178 mmol) was taken in ethanol (2 ml). To this was added NaBH4 (0.02 mg, 0.525 mmol) at 0° C. and stirred at room temperature for 2 hours. The reaction mixture was quenched with saturated NH4Cl and solvent was concentrated under reduced pressure. Aqueous layer was extracted with ethyl acetate and organic layer was washed with brine, dried over Na2SO4 and concentrated under reduced pressure. The residue was purified by preparative HPLC using 1% methanol in dichloromethane as solvent system to give the product as off white solid (0.04 g) in 85% yield.

Workup

  1. customThe reaction mixture was quenched with saturated NH4Cl and solvent
  2. concentrationwas concentrated under reduced pressure
  3. extractionAqueous layer was extracted with ethyl acetate and organic layer
  4. washwas washed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-82ba9d2b71b6439eb8dafef31dc2a779
Source dataset
uspto-grants-2014_08
Patent number
US08796290B2

Reaction notes

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