Benzylamine → N4-Benzyl-3-bromo-1-methyl-1H-pyrazolo[3,4-d]pyrimidine-4,6-diamine

HRID 1396580Notes

Reaction equation

[Br:1][C:2]1[C:10]2[C:5](=[N:6][C:7]([NH2:12])=[N:8][C:9]=2Cl)[N:4]([CH3:13])[N:3]=1.[CH2:14]([NH2:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>CN(C=O)C>[CH2:14]([NH:21][C:9]1[N:8]=[C:7]([NH2:12])[N:6]=[C:5]2[N:4]([CH3:13])[N:3]=[C:2]([Br:1])[C:10]=12)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

Conditions

Temperature: 40 °C

Procedure

3-Bromo-4-chloro-1-methyl-1H-pyrazolo[3,4-d]pyrimidin-6-ylamine (Intermediate 14) (160 mg, 0.61 mmol), benzylamine (0.2 ml, 1.83 mmol) and DMF (5 ml) are mixed together and heated at 40° C. overnight. After cooling to room temperature the solvent is removed in vacuo and the residue is dissolved in methanol (30 ml) and passed through an Isolute™ CBA column (silica based carboxylic acid sorbent). Silica gel is added to the filtrate, the solvent is removed in vacuo and the resulting residue is flash chromatographed eluting with EtOAc:iso-hexanes (4:6) and then increasing to EtOAc:iso-hexanes (1:1). The appropriate fractions are collected and concentrated in vacuo to afford the title compound.

Workup

temperatureAfter cooling to room temperature the solvent
customis removed in vacuo
dissolutionthe residue is dissolved in methanol (30 ml)
additionSilica gel is added to the filtrate
customthe solvent is removed in vacuo
customchromatographed
washeluting with EtOAc:iso-hexanes (4:6)
temperatureincreasing to EtOAc:iso-hexanes (1:1)
customThe appropriate fractions are collected
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-5577f1745fc241ddb4946e2bc09aef1b
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08901134B2

Reaction notes

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