Potassium Carbonate → HCID 44622155, compound

HRID 1931696Notes

Reaction equation

HRID 1931696 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].[OH:24][C:25]1[C:26]([CH3:31])=[N:27][CH:28]=[CH:29][CH:30]=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:24][C:25]4[C:26]([CH3:31])=[N:27][CH:28]=[CH:29][CH:30]=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 707192-Methylpyridin-3-olHCID 57964905Tert-butyl 4-(4-chloro-1H-pyrazolo[3,4-D]pyrimidin-1-YL)piperidine-1-carboxylate2×

Product 1

HCID 44622155HCID 44622155, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 4-(4-chloro-pyrazolo[3,4-d]pyrimidin-1-yl)-piperidine-1-carboxylic acid tert-butyl ester (Intermediate 19; 3.00 g, 8.9 mmol), 3-hydroxy-2-methylpyridine (Aldrich Chemical Company, Inc., Milwaukee, Wis., USA 1.26 g, 12 mmol), and potassium carbonate (1.59 g, 11.5 mmol) in dimethylformamide (30 mL) was heated at 100° C. overnight. The solvent was evaporated under high vacuum. Water (50 mL) and dichloromethane (50 mL) were added. The layers were separated and the organic layer was washed twice with water and then evaporated to dryness to give 4-[4-(2-methyl-pyridin-3-yloxy)-pyrazolo[3,4-d]pyrimidin-1-yl]-piperidine-1-carboxylic acid tert-butyl ester (3.24 g, 89%). A sample of this material (500 mg) was purified by silica gel column chromatography, eluting with 0-75% ethyl acetate/hexanes, to give 4-[4-(2-methyl-pyridin-3-yloxy)-pyrazolo[3,4-d]pyrimidin-1-yl]-piperidine-1-carboxylic acid tert-butyl ester (381 mg, 10%) as a white powder. 1H NMR (300 MHz, CDCl3) δ 1.49 (s, 9H), 1.97-2.06 (m, 2H), 2.20-2.34 (m, 2H), 2.47 (s, 3H), 2.91-3.05 (m, 2H), 4.26-4.39 (m, 2H), 4.91-5.03 (m, 1H), 7.27-7.29 (m, 1H), 7.50-7.55 (m, 1H), 8.07 (s, 1H), 8.48-8.51 (m, 2H). Mass spectrum MH+=411. HRMS Calcd. For C21H27N6O3 (MH+): 411.2139. Found: 411.2137.

Workup

  1. customThe solvent was evaporated under high vacuum
  2. additionWater (50 mL) and dichloromethane (50 mL) were added
  3. customThe layers were separated
  4. washthe organic layer was washed twice with water
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-4abb1c1eb67b48d390933e7ec4e0a809
Source dataset
uspto-grants-2012_05
Patent number
US08188098B2

Reaction notes

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