Potassium Carbonate → HCID 74766963, compound

HRID 923304Notes

Reaction equation

HRID 923304 reaction equation
Cl[C:2]1[N:7]=[CH:6][N:5]=[C:4]2[N:8]([CH2:11][CH2:12][N:13]3[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]3)[N:9]=[CH:10][C:3]=12.[C:19]1(B(O)O)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C([O-])([O-])=O.[K+].[K+]>C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:19]1([C:2]2[N:7]=[CH:6][N:5]=[C:4]3[N:8]([CH2:11][CH2:12][N:13]4[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]4)[N:9]=[CH:10][C:3]=23)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 66827Phenylboronic AcidHCID 86721084HCID 86721084, compound

Product 1

HCID 74766963HCID 74766963, compoundYield 33%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 4-chloro-1-(2-(piperidin-1-yl)ethyl)-1H-pyrazolo[3,4-d]pyrimidine (50 mg, 0.19 mmol), phenylboronic acid (73 mg, 0.60 mmol) and anhydrous K2CO3 (82 mg, 0.59 mmol) in toluene (3 mL) was introduced in a microwave vial. It was degassed by argon for 30 minutes followed by the addition of Pd(PPh3)4 (4.0 mg, 0.003 mmol) after which the mixture was degassed for 10 additional minutes. The mixture was stirred at 150° C. for 30 min under microwave irradiation (150 W). After cooling to rt, the mixture was filtered on decalite and the solvent was removed at reduced pressure. The crude was purified by flash chromatography to provide 4-phenyl-1-(2-(piperidin-1-yl)ethyl)-1H-pyrazolo[3,4-d]pyrimidine as a white solid (19.1 mg, 0.06 mmol, 33%).

Workup

  1. additionwas introduced in a microwave vial
  2. customIt was degassed by argon for 30 minutes
  3. customwas degassed for 10 additional minutes
  4. temperatureAfter cooling to rt
  5. filtrationthe mixture was filtered on decalite
  6. customthe solvent was removed at reduced pressure
  7. customThe crude was purified by flash chromatography

Sources & evidence

ORD record
ord-c6cb4c466e7f47a38c03d3846740ae56
Source dataset
uspto-grants-2016_03
Patent number
US09278974B2

Reaction notes

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