Potassium Carbonate → HCID 57964938, compound

HRID 1931698Notes

Reaction equation

HRID 1931698 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][CH:20]=[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].[CH3:24][C:25]1[C:30]([OH:31])=[CH:29][CH:28]=[C:27]([CH3:32])[N:26]=1.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][CH:20]=[N:21][C:22]([O:31][C:30]4[C:25]([CH3:24])=[N:26][C:27]([CH3:32])=[CH:28][CH:29]=4)=[C:17]3[CH:16]=[N:15]2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 707322,6-Dimethyl-3-pyridinolHCID 57964905Tert-butyl 4-(4-chloro-1H-pyrazolo[3,4-D]pyrimidin-1-YL)piperidine-1-carboxylate2×

Product 1

HCID 57964938HCID 57964938, compoundYield 74.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-[4-(2,6-Dimethyl-pyridin-3-yloxy)-pyrazolo[3,4-d]pyrimidin-1-yl]-piperidine-1-carboxylic acid tert-butyl ester (41 mg, 65%) was prepared using the procedure described for the preparation of Example 96, by the reaction of 4-(4-chloro-pyrazolo[3,4-d]pyrimidin-1-yl)-piperidine-1-carboxylic acid tert-butyl ester (Intermediate 19; 50 mg, 0.15 mmol) with 2,6-dimethyl-3-hydroxypyridine (Apollo Scientific Ltd., Stockport, Cheshire, UK; 16 mg) in the presence of potassium carbonate (27 mg, 0.19 mmol) in dimethylformamide (2 mL). Mass spectrum (ES) MH+=425. HRMS Calcd. for C22H29N6O3 (MH+): 425.2296. Found: 425.2294.

Sources & evidence

ORD record
ord-107529827d364e0f8481139ca1c09e0c
Source dataset
uspto-grants-2012_05
Patent number
US08188098B2

Reaction notes

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