Sodium borohydride → 6-(Hydroxymethyl)-2-(4-phenoxyphenyl)-4,5,6,7-tetrahydro pyrazolo[1,5-a]pyrimidine-3-carbonitrile

HRID 64362Notes

Reaction equation

HRID 64362 reaction equation
[C:1]([C:3]1[C:4]([C:17]2[CH:22]=[CH:21][C:20]([O:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[CH:19][CH:18]=2)=[N:5][N:6]2[CH:11]=[C:10]([C:12](OCC)=[O:13])[CH:9]=[N:8][C:7]=12)#[N:2].[BH4-].[Na+]>C(Cl)Cl.CO>[OH:13][CH2:12][CH:10]1[CH2:11][N:6]2[N:5]=[C:4]([C:17]3[CH:22]=[CH:21][C:20]([O:23][C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)=[CH:19][CH:18]=3)[C:3]([C:1]#[N:2])=[C:7]2[NH:8][CH2:9]1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 117668240Ethyl 3-cyano-2-(4-phenoxyphenyl)pyrazolo[1,5-a]pyrimidine-6-carboxylate

Product 1

HCID 1369281006-(Hydroxymethyl)-2-(4-phenoxyphenyl)-4,5,6,7-tetrahydro pyrazolo[1,5-a]pyrimidine-3-carbonitrileYield 111%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of ethyl 3-cyano-2-(4-phenoxyphenyl)pyrazolo[1,5-a]pyrimidine-6-carboxylate (250 mg, 0.65 mmol) in DCM (5 mL) and CH3OH (5 mL) was added NaBH4 (250 mg, 6.5 mmol). After stirring at RT for 16 hr, the mixture was partitioned between DCM/CH3OH (100 mL/5 mL) and brine (100 mL). The organic layer was separated from aqueous layers, dried over Na2SO4 and concentrated to afford 250 mg (100%) of 6-(hydroxymethyl)-2-(4-phenoxyphenyl)-4,5,6,7-tetrahydro pyrazolo[1,5-a]pyrimidine-3-carbonitrile. MS (ESI) m/e [M+1]+346.9.

Workup

  1. customthe mixture was partitioned between DCM/CH3OH (100 mL/5 mL) and brine (100 mL)
  2. customThe organic layer was separated from aqueous layers
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-a0f450ec046d4e26a96c4c72cf8f6b19
Source dataset
uspto-grants-2016_09
Patent number
US09447106B2

Reaction notes

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