Potassium Carbonate → HCID 57964990, compound

HRID 1931776Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([N:14]2[C:18]3=[N:19][C:20]([NH2:24])=[N:21][C:22](Cl)=[C:17]3[CH:16]=[N:15]2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH:25][C:26]1[CH:33]=[CH:32][CH:31]=[CH:30][C:27]=1[C:28]#[N:29].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([N:14]2[C:18]3=[N:19][C:20]([NH2:24])=[N:21][C:22]([O:25][C:26]4[CH:33]=[CH:32][CH:31]=[CH:30][C:27]=4[C:28]#[N:29])=[C:17]3[CH:16]=[N:15]2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of: 4-(6-amino-4-chloro-pyrazolo[3,4-d]pyrimidin-1-yl)-piperidine-1-carboxylic acid tert-butyl ester (Intermediate 33; 224 mg, 0.64 mmol), 2-hydroxybenzonitrile (available from Alfa Aesar, Ward Hill, Mass., USA; 95.2 mg, 0.8 mmol), and potassium carbonate (220 mg, 1.6 mmol) in N,N-dimethylformamide (5 mL) was heated at 80° C. for 3 h, and then cooled. Volatiles were evaporated and the residue was chromatographed (50-65% ethyl acetate/hexanes) to give 4-[6-Amino-4-(2-cyano-phenoxy)-pyrazolo[3,4-d]pyrimidin-1-yl]-piperidine-1-carboxylic acid tert-butyl ester (261 mg, 94%) as a white solid.

Workup

temperaturecooled
customVolatiles were evaporated
customthe residue was chromatographed (50-65% ethyl acetate/hexanes)

Sources & evidence

ORD record: ord-c17c3d50b8f64afb803fd47c1aaaa46a
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08188098B2

Reaction notes

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