Acetic Acid → 1H-Pyrazolo[3,4-d]pyrimidin-4-amine

HRID 432285Notes

Reaction equation

HRID 432285 reaction equation
I[C:2]1[C:10]2[C:5](=[N:6][CH:7]=[N:8][C:9]=2[NH2:11])[N:4](C2CCNCC2)[N:3]=1.CN1CCC(=O)CC1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C.C(=O)(O)[O-].[Na+]>ClCCCl>[NH:4]1[C:5]2=[N:6][CH:7]=[N:8][C:9]([NH2:11])=[C:10]2[CH:2]=[N:3]1

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 740491-Methyl-4-piperidoneHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 223466933-Iodo-1-(piperidin-4-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine

Product 1

HCID 754201H-Pyrazolo[3,4-d]pyrimidin-4-amineYield 304.4%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

3-Iodo-1-(4-piperidyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine (2.00 g, 5.81 mmol), 1-methyl-4-piperidone (2.14 mL, 17.42 mmol), sodium triacetoxyborohydride (2.45 g, 11.62 mmol) and glacial acetic acid (1.05 g, 17.42 mmol) were mixed with 1,2-dichloroethane (75 mL). The reaction mixture was stirred at room temperature for 6 hours and saturated sodium bicarbonate solution was added to adjust the PH to about 8. The solid was collected by filtration to give 3-Iodo-1-[1-(1-methylpiperidin-4-yl)]-piperidin-4-yl]-1H-pyrazolo[3,4-d]pyrimidin-4-amine (2.39 g, 93%). 1H NMR (DMSO-d6) δ 1.52 (m, 2H), 1.75 (m, 2H), 1.87 (m, 2H), 2.05 (m, 4H), 2.24 (s, 3H), 2.28 (m, 3H), 2.91 (m, 2H), 3.00 (m, 2H), 4.55 (m, 1H), 8.18 (s, 1H).

Workup

  1. filtrationThe solid was collected by filtration

Sources & evidence

ORD record
ord-6f92c2c7d4124de581cc076ae02e130c
Source dataset
uspto-grants-2003_12
Patent number
US06660744B1

Reaction notes

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