Sodium borohydride → HCID 15958148, compound

HRID 270955Notes

Reaction equation

HRID 270955 reaction equation
[BH4-].[Na+].[CH2:3]([O:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[CH:18]=[N:19][C:20]3[N:21]([N:29]=[CH:30][C:31]=3[CH:32]=[O:33])[C:22]=2[CH:23]2[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]2)=[CH:13][CH:12]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>CO.O1CCCC1>[CH2:3]([O:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[CH:18]=[N:19][C:20]3[N:21]([N:29]=[CH:30][C:31]=3[CH2:32][OH:33])[C:22]=2[CH:23]2[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]2)=[CH:13][CH:12]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 15958110HCID 15958110, compound

Product 1

HCID 15958148HCID 15958148, compoundYield 47%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 4.4 mg (0.115 mmol) of sodium borohydride (NaBH4) in 2 mL of methanol (MeOH) was added a solution of 35 mg (0.104 mmol) of 6-(4-benzyloxy-phenyl)-7-cyclohexyl-pyrazolo[1,5-a]pyrimidine-3-carbaldehyde in 3 mL of tetrahydrofuran (THF) and the resulting mixture was stirred at rt for 30 min when analysis by TLC indicated complete conversion of starting material to product. The reaction mixture was quenched by the addition of saturated ammonium chloride solution, and extracted with ethyl acetate. The combined organic extracts were washed with brine, dried over sodium sulfate and evaporated to give (after lyophilization) 20 mg (47% yield) of [6-(4-benzyloxy-phenyl)-7-cyclohexyl-pyrazolo[1,5-a]pyrimidin-3-yl]-methanol (479) as a white solid (85% purity) as indicated by 1H NMR (containing small traces of starting material); LC-MS—calcd for C26H27N3O2 [M++H]+: 414.21, found: 414.2.

Workup

  1. customThe reaction mixture was quenched by the addition of saturated ammonium chloride solution
  2. extractionextracted with ethyl acetate
  3. washThe combined organic extracts were washed with brine
  4. dry with materialdried over sodium sulfate
  5. customevaporated

Sources & evidence

ORD record
ord-ace0e07fe80c48bf8ece5696a7bea962
Source dataset
uspto-grants-2008_11
Patent number
US07449488B2

Reaction notes

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