Sodium borohydride → 7-(2-(Methylamino)phenyl)-2-(4-phenoxy phenyl)-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidine-3-carbonitrile

HRID 64278Notes

Reaction equation

HRID 64278 reaction equation
[CH3:1][NH:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[N:14]2[N:15]=[C:16]([C:20]3[CH:25]=[CH:24][C:23]([O:26][C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)=[CH:22][CH:21]=3)[C:17]([C:18]#[N:19])=[C:13]2[N:12]=[CH:11][CH:10]=1.[BH4-].[Na+]>CCO>[CH3:1][NH:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH:9]1[N:14]2[N:15]=[C:16]([C:20]3[CH:25]=[CH:24][C:23]([O:26][C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)=[CH:22][CH:21]=3)[C:17]([C:18]#[N:19])=[C:13]2[NH:12][CH2:11][CH2:10]1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 1176680947-(2-(Methylamino)phenyl)-2-(4-phenoxyphenyl)pyrazolo[1,5-a]pyrimidine-3-carbonitrile

Product 1

HCID 1369280907-(2-(Methylamino)phenyl)-2-(4-phenoxy phenyl)-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidine-3-carbonitrileYield 56.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 7-(2-(methylamino)phenyl)-2-(4-phenoxyphenyl)pyrazolo[1,5-a]pyrimidine-3-carbonitrile (250 mg, 0.6 mmol) in 10 mL EtOH was added NaBH4 (100 mg). The reaction mixture was stirred at it for 15 hr, and then concentrated to remove EtOH. The residue was partitioned between 30 mL of water and 30 mL of EA. The organic layer was concentrated. The residue was dissolved in 10 mL of MeOH, followed by 10% w/w Pd/C (50 mg). The reaction mixture was stirred at it under 1 atm. of H2 for 15 hr. Then, the mixture was filtered. The filtrate was concentrated and purified by the flash chromatography (PE/EA=1/1) to give the product as a white solid (144 mg, yield: 56.5%). MS (ESI) m/e [M+1]+ 421.9.

Workup

  1. concentrationconcentrated
  2. customto remove EtOH
  3. customThe residue was partitioned between 30 mL of water and 30 mL of EA
  4. concentrationThe organic layer was concentrated
  5. dissolutionThe residue was dissolved in 10 mL of MeOH
  6. stirringThe reaction mixture was stirred at it under 1 atm. of H2 for 15 hr
  7. filtrationThen, the mixture was filtered
  8. concentrationThe filtrate was concentrated
  9. custompurified by the flash chromatography (PE/EA=1/1)

Sources & evidence

ORD record
ord-2528b3ab255b46ddafed40e8067ee9ee
Source dataset
uspto-grants-2016_09
Patent number
US09447106B2

Reaction notes

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