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

HRID 64362노트

반응식

HRID 64362 반응식
[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

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 887Methanol용매HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-a0f450ec046d4e26a96c4c72cf8f6b19
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09447106B2

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