Potassium Carbonate → HCID 71225444, compound

HRID 1258419Notes

Reaction equation

HRID 1258419 reaction equation
[NH2:1][C:2]1[N:7]=[C:6](Cl)[CH:5]=[C:4]([CH3:9])[N:3]=1.[N:10]1[CH:15]=[CH:14][C:13](B(O)O)=[CH:12][C:11]=1[CH3:19].C(=O)([O-])[O-].[K+].[K+]>COCCOC.O.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>[CH3:9][C:4]1[CH:5]=[C:6]([C:13]2[CH:14]=[CH:15][N:10]=[C:11]([CH3:19])[CH:12]=2)[N:7]=[C:2]([NH2:1])[N:3]=1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 218102-Amino-4-chloro-6-methylpyrimidineHCID 41926642-Methylpyridine-4-boronic acid

Product 1

HCID 71225444HCID 71225444, compound

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

A mixture of 2.00 g (13.9 mmol) 2-amino-4-chloro-6-methylpyrimidine, 2.48 g (18.1 mmol) 2-picoline-4-boronic acid, 0.43 g (2.8 mmol) tetrakis(triphenylphosphine)palladium(0) and 3.85 g (27.9 mmol) potassium carbonate in 40 mL 1,2-dimethoxyethane and 4 mL water is heated to reflux temperature and stirred overnight. The reaction mixture is concentrated under reduced pressure, water is added and the precipitated product is filtered off and dried in vacuo at 40° C. Yield: 1.94 g (69%).

Workup

  1. temperatureis heated
  2. temperatureto reflux temperature
  3. concentrationThe reaction mixture is concentrated under reduced pressure, water
  4. additionis added
  5. filtrationthe precipitated product is filtered off
  6. customdried in vacuo at 40° C

Sources & evidence

ORD record
ord-b3e0d2cd65614f038d5a0a2abe9f949e
Source dataset
uspto-grants-2013_06
Patent number
US08466162B2

Reaction notes

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