Sodium Carbonate → HCID 67286958, compound

HRID 1410404Notes

Reaction equation

HRID 1410404 reaction equation
Cl[C:2]1[C:7]([CH3:8])=[C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[CH3:15])[N:5]=[CH:4][N:3]=1.[C:16]1(B(O)O)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(=O)([O-])[O-].[Na+].[Na+]>C1(C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)[Pd][P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O.C(#N)C>[CH3:8][C:7]1[C:2]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[N:3][CH:4]=[N:5][C:6]=1[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH3:15]

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 65647653HCID 65647653, compound

Product 1

HCID 67286958HCID 67286958, compoundYield 87%

Reagents, catalysts & solvents 3

HCID 178419050HCID 178419050, compoundCatalystHCID 962WaterSolvent2×HCID 6342AcetonitrileSolvent

Procedure

Next, into a recovery flask equipped with a reflux pipe were put 1.9 g of 4-chloro-5-methyl-6-(2-methylphenyl)pyrimidine obtained in Step 1, 1.7 g of phenylboronic acid, 1.1 g of sodium carbonate, 0.105 g of bis(triphenylphosphine)palladium (II) dichloride (abbreviation: Pd(PPh3)2Cl2), 20 mL of water, and 20 mL of acetonitrile, and the air in the flask was replaced with argon. This reaction container was heated by irradiation with microwaves (2.45 GHz, 100 W) for 1 hour. After that, water was added to this solution and an organic layer was extracted with dichloromethane. The obtained organic layer was washed with saturated aqueous solution of sodium hydrogen carbonate, water, and saturated saline, and was dried with magnesium sulfate. The solution after drying was filtered. The solvent of this solution was distilled off, and then the obtained residue was purified by silica gel column chromatography using hexane and ethyl acetate as a developing solvent in a ratio of 9:1 and the obtained fraction was concentrated, so that 5-methyl-6-(2-methylphenyl)-4-phenylpyrimidine was obtained (a white solid, yield of 87%). A synthesis scheme (q-2) of Step 2 is shown below.

Workup

  1. customNext, into a recovery flask equipped with a reflux pipe
  2. temperatureThis reaction container was heated by irradiation with microwaves (2.45 GHz, 100 W) for 1 hour
  3. extractionan organic layer was extracted with dichloromethane
  4. washThe obtained organic layer was washed with saturated aqueous solution of sodium hydrogen carbonate, water, and saturated saline
  5. dry with materialwas dried with magnesium sulfate
  6. customThe solution after drying
  7. filtrationwas filtered
  8. distillationThe solvent of this solution was distilled off
  9. customthe obtained residue was purified by silica gel column chromatography
  10. concentrationthe obtained fraction was concentrated, so that 5-methyl-6-(2-methylphenyl)-4-phenylpyrimidine
  11. customwas obtained (a white solid, yield of 87%)
  12. customA synthesis scheme (q-2) of Step 2

Sources & evidence

ORD record
ord-27879db570794f0394592ccfeb1eb5a8
Source dataset
uspto-grants-2014_12
Patent number
US08921548B2

Reaction notes

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