Sodium triacetoxyborohydride → 1-{1-[4-(6-phenyl-imidazo[1,2-a]pyrimidin-7-yl)-benzyl]-piperidin-4-yl}-1H-pyrazolo[3,4-d]pyrimidin-4-ylamine

HRID 1851263Notes

Reaction equation

HRID 1851263 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]([CH:13]=[CH:14][N: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]([CH:13]=[CH:14][N:15]=3)[CH:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 3

HCID 5049666Sodium triacetoxyborohydrideHCID 577139461-piperidin-4-yl-1H-pyrazolo[3,4-d]pyrimidin-4-amineHCID 866306554-(6-Phenylimidazo[1,2-a]pyrimidin-7-yl)benzaldehyde

Product 1

HCID 687521981-{1-[4-(6-phenyl-imidazo[1,2-a]pyrimidin-7-yl)-benzyl]-piperidin-4-yl}-1H-pyrazolo[3,4-d]pyrimidin-4-ylamineYield 41.9%

Procedure

300 mg (1 mmol) 4-(6-phenylimidazo[1,2-a]pyrimidin-7-yl)benzaldehyde and 306 mg (1.20 mmol) 1-piperidine-4-yl-1H-pyrazolo[3,4-d]pyrimidin-4-ylamine were reacted for four days (additional NaBH(OAc)3 has been added after four, six, eight, 24 and 28 hours (two equivalents each)) at room temperature and purified as previously described. 210 mg of the desired compound were obtained.

Workup

  1. custompurified

Sources & evidence

ORD record
ord-62718586e3ff4af4a0071273a8422ea6
Source dataset
uspto-grants-2015_02
Patent number
US08957064B2

Reaction notes

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