Ammonia → HCID 178508615, compound

HRID 432237Notes

Reaction equation

C([O:8][CH2:9][C@H:10]1[CH2:13][C@H:12]([N:14]2[C:18]3=[N:19][CH:20]=[N:21][C:22]([NH2:23])=[C:17]3[C:16]([C:24]3[CH:29]=[CH:28][C:27]([O:30][C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=4)=[CH:26][CH:25]=3)=[N:15]2)[CH2:11]1)C1C=CC=CC=1.B(Cl)(Cl)Cl.N>ClCCl.CO>[NH2:23][C:22]1[N:21]=[CH:20][N:19]=[C:18]2[N:14]([C@H:12]3[CH2:11][C@H:10]([CH2:9][OH:8])[CH2:13]3)[N:15]=[C:16]([C:24]3[CH:25]=[CH:26][C:27]([O:30][C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=4)=[CH:28][CH:29]=3)[C:17]=12

Participants

Conditions

Temperature: -78 °C

Procedure

A solution of trans 1-{3-[(benzyloxy)methyl]cyclobutyl}-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine (0.244 g, 0.00051 mol) in dichloromethane (10 mL) was cooled to −78° C. and a solution of 1.0 M boron trichloride in dichloromethane (1.53 mL, 0.00153 mol) was added dropwise, keeping the temperature less than −70° C. The reaction mixture was stirred seven hours at −78° C., after which time a 8 M solution of ammonia in methanol (1.5 mL) was added . The solvent was removed in vacuo. The residue was purified by flash column chromatography on silica using dichloromethane/methanol (93:7). The solvent was removed in vacuo to give to give trans 3-[4-amino-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]cyclobutylmethanol (0.192 g, 0.00049 mol) as a white solid.

Workup

customthe temperature less than −70° C
customThe solvent was removed in vacuo
customThe residue was purified by flash column chromatography on silica
customThe solvent was removed in vacuo
customto give

Sources & evidence

ORD record: ord-33b50eac03e842e69f9881339961918f
Source dataset: uspto-grants-2003_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06660744B1

Reaction notes

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