Sodium triacetoxyborohydride → 1-{1-[4-(6-phenyl-pyrazolo[1,5-a]pyrimidin-5-yl)-benzyl]-piperidin-4-yl}-1H-pyrazolo[3,4-d]pyrimidin-4-ylamine

HRID 1851271노트

반응식

HRID 1851271 반응식
[C:1]1([C:7]2[C:8]([C:16]3[CH:23]=[CH:22][C:19]([CH:20]=O)=[CH:18][CH:17]=3)=[N:9][C:10]3[N:11]([N:13]=[CH:14][CH:15]=3)[CH:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH:24]1[CH2:29][CH2:28][CH:27]([N:30]2[C:34]3=[N:35][CH:36]=[N:37][C:38]([NH2:39])=[C:33]3[CH:32]=[N:31]2)[CH2:26][CH2:25]1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>>[C:1]1([C:7]2[C:8]([C:16]3[CH:23]=[CH:22][C:19]([CH2:20][N:24]4[CH2:29][CH2:28][CH:27]([N:30]5[C:34]6=[N:35][CH:36]=[N:37][C:38]([NH2:39])=[C:33]6[CH:32]=[N:31]5)[CH2:26][CH2:25]4)=[CH:18][CH:17]=3)=[N:9][C:10]3[N:11]([N:13]=[CH:14][CH:15]=3)[CH:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

참가 물질

4

반응물 3

HCID 5049666Sodium triacetoxyborohydride2회HCID 577139461-piperidin-4-yl-1H-pyrazolo[3,4-d]pyrimidin-4-amine2회HCID 866306654-(6-Phenylpyrazolo[1,5-a]pyrimidin-5-yl)benzaldehyde

생성물 1

HCID 687527071-{1-[4-(6-phenyl-pyrazolo[1,5-a]pyrimidin-5-yl)-benzyl]-piperidin-4-yl}-1H-pyrazolo[3,4-d]pyrimidin-4-ylamine수율 25.6%

실험 절차

250 mg (0.84 mmol) 4-(6-phenylpyrazolo[1,5-a]pyrimidin-5-yl)benzaldehyde and 257 mg (1 mmol) 1-piperidine-4-yl-1H-pyrazolo[3,4-d]pyrimidin-4-ylamine were treated as previously described. Additional NaBH(OAc)3 has been added after one, two and three hours (two equivalents each). After a further stirring at room temperature additional 26 mg 1-piperidine-4-yl-1H-pyrazolo[3,4-d]pyrimidin-4-ylamine and two equivalents NaBH(OAc)3 were added. After stirring overnight and two further additions of NaBH(OAc)3 the solvents were evaporated. Workup und purification yields 108 mg of the desired compound.

후처리

  1. additionwere added
  2. customtwo further additions of NaBH(OAc)3 the solvents were evaporated
  3. custompurification

출처 및 근거

ORD 기록
ord-16bac07ea44847c2bedcfcadcc192982
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08957064B2

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