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 1851271Notes

Reaction equation

HRID 1851271 reaction equation
[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

Participants

4

Reactant 3

HCID 5049666Sodium triacetoxyborohydride2×HCID 577139461-piperidin-4-yl-1H-pyrazolo[3,4-d]pyrimidin-4-amine2×HCID 866306654-(6-Phenylpyrazolo[1,5-a]pyrimidin-5-yl)benzaldehyde

Product 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-ylamineYield 25.6%

Procedure

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.

Workup

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

Sources & evidence

ORD record
ord-16bac07ea44847c2bedcfcadcc192982
Source dataset
uspto-grants-2015_02
Patent number
US08957064B2

Reaction notes

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