Water → 6-Nitro-2-(4-phenoxyphenyl)-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidine-3-carbonitrile

HRID 64358Notes

Reaction equation

HRID 64358 reaction equation
[N+:1]([C:4]1[CH:5]=[N:6][C:7]2[N:8]([N:10]=[C:11]([C:15]3[CH:20]=[CH:19][C:18]([O:21][C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)=[CH:17][CH:16]=3)[C:12]=2[C:13]#[N:14])[CH:9]=1)([O-:3])=[O:2].[BH4-].[Na+].O>C(O)C.C(Cl)Cl>[N+:1]([CH:4]1[CH2:9][N:8]2[N:10]=[C:11]([C:15]3[CH:16]=[CH:17][C:18]([O:21][C:22]4[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=4)=[CH:19][CH:20]=3)[C:12]([C:13]#[N:14])=[C:7]2[NH:6][CH2:5]1)([O-:3])=[O:2]

Participants

6

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 117668253HCID 117668253, compound

Product 1

HCID 1369280626-Nitro-2-(4-phenoxyphenyl)-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidine-3-carbonitrileYield 55.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 6-nitro-2-(4-phenoxyphenyl)pyrazolo[1,5-a]pyrimidine-3-carbonitrile (90 mg, 0.25 mmol) in 2 mL of ethanol and 2 mL of DCM was added NaBH4 (19 mg, 0.5 mmol) at RT. After stirring at RT for 30 min, 5 mL of water was added. The mixture was concentrated. The residue was partitioned between 50 mL of DCM and 50 mL of brine. The combined organic layers were washed with brine (50 mL×2), dried over Na2SO4 and concentrated to afford 50 mg of 6-nitro-2-(4-phenoxyphenyl)-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidine-3-carbonitrile (55%) as a yellow solid. MS (ESI) m/e [M+1]+ 362.1.

Workup

  1. concentrationThe mixture was concentrated
  2. customThe residue was partitioned between 50 mL of DCM and 50 mL of brine
  3. washThe combined organic layers were washed with brine (50 mL×2)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-7180aa25459f4913a5a24e38de8fab99
Source dataset
uspto-grants-2016_09
Patent number
US09447106B2

Reaction notes

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