Potassium Carbonate → HCID 57964936, compound

HRID 1931694Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH:10]([N:14]2[C:18]3=[N:19][CH:20]=[N:21][C:22](Cl)=[C:17]3[CH:16]=[N:15]2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH:24][C:25]1[CH:32]=[CH:31][CH:30]=[CH:29][C:26]=1[C:27]#[N:28].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH:10]([N:14]2[C:18]3=[N:19][CH:20]=[N:21][C:22]([O:24][C:25]4[CH:32]=[CH:31][CH:30]=[CH:29][C:26]=4[C:27]#[N:28])=[C:17]3[CH:16]=[N:15]2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 160 °C

Procedure

A mixture of 3-(4-Chloro-pyrazolo[3,4-d]pyrimidin-1-yl)-piperidine-1-carboxylic acid tert-butyl ester (Intermediate 32; 40 mg, 0.12 mmol), 2-hydroxybenzonitrile (available from Aldrich Chemical Company, Inc., Milwaukee, Wis., USA 15.5 mg, 0.13 mmol) and potassium carbonate (15 mg, 0.25 mmol) in dimethylformamide (0.6 mL) was heated in a microwave oven at 160° C. for 10 min. The reaction mixed was cooled and filtered. Volatiles were evaporated and the residue purified twice by chromatography on silica gel, eluting first with 25% ethyl acetate/hexanes and then with 20% ethyl acetate/hexanes to give 3-[4-(2-cyano-phenoxy)-pyrazolo[3,4-d]pyrimidin-1-yl]-piperidine-1-carboxylic acid tert-butyl ester (22 mg, 47%) as a viscous oil

Workup

additionThe reaction mixed
temperaturewas cooled
filtrationfiltered
customVolatiles were evaporated
customthe residue purified twice by chromatography on silica gel
washeluting first with 25% ethyl acetate/hexanes

Sources & evidence

ORD record: ord-218aaa4ec6784243b06026c6caefa16f
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08188098B2

Reaction notes

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