Hydrochloric Acid → (R)-1-[6-(2,4-Difluoro-phenoxy)-1H-pyrazolo[3,4-d]pyrimidin-4-ylamino]-propan-2-ol

HRID 230185Notes

Reaction equation

[F:1][C:2]1[CH:30]=[C:29]([F:31])[CH:28]=[CH:27][C:3]=1[O:4][C:5]1[N:10]=[C:9]2[N:11](COCC[Si](C)(C)C)[N:12]=[CH:13][C:8]2=[C:7]([NH:22][CH2:23][C@H:24]([OH:26])[CH3:25])[N:6]=1.Cl>CO>[F:1][C:2]1[CH:30]=[C:29]([F:31])[CH:28]=[CH:27][C:3]=1[O:4][C:5]1[N:10]=[C:9]2[NH:11][N:12]=[CH:13][C:8]2=[C:7]([NH:22][CH2:23][C@H:24]([OH:26])[CH3:25])[N:6]=1

Participants

Conditions

Temperature: 80 °C

Procedure

(R)-1-[6-(2,4-Difluoro-phenoxy)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrazolo[3,4-d]pyrimidin-4-ylamino]-propan-2-ol (258 mg) was dissolved in 8 mL MeOH, and 0.6 mL of 6M HCl was added. The reaction mixture was heated to 80° C. for 3.5 hours, then cooled. The reaction mixture was quenched by addition to water, and was partitioned between water and ethyl acetate. The organic layer was separated, dried over MgSO4, filtered, and evaporated under reduced pressure. The residue was purified by flash chromatography (10% MeOH in methylene chloride) to give 116 mg of (R)-1-[6-(2,4-Difluoro-phenoxy)-1H-pyrazolo[3,4-d]pyrimidin-4-ylamino]-propan-2-ol. Mass Spec. M+H=322.

Workup

temperaturecooled
customThe reaction mixture was quenched by addition to water
customwas partitioned between water and ethyl acetate
customThe organic layer was separated
dry with materialdried over MgSO4
filtrationfiltered
customevaporated under reduced pressure
customThe residue was purified by flash chromatography (10% MeOH in methylene chloride)

Sources & evidence

ORD record: ord-1e656437a833460b8bc6867107719d5c
Source dataset: uspto-grants-2009_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07566708B2

Reaction notes

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