Sodium Carbonate → 4-Methyl-6-phenylpyrimidine

HRID 1525523Notes

Reaction equation

HRID 1525523 reaction equation
Cl[C:2]1[CH:7]=[C:6]([CH3:8])[N:5]=[CH:4][N:3]=1.[C:9]1(B(O)O)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C(=O)([O-])[O-].[Na+].[Na+]>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.ClCCl.O.C(#N)C>[CH3:8][C:6]1[CH:7]=[C:2]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[N:3]=[CH:4][N:5]=1

Participants

8

Reactant 3

HCID 10340Sodium Carbonate2×HCID 66827Phenylboronic Acid2×HCID 5817964-Chloro-6-methylpyrimidine

Product 1

HCID 5984294-Methyl-6-phenylpyrimidineYield 46%

Reagents, catalysts & solvents 4

HCID 178418476HCID 178418476, compoundCatalyst2×HCID 962WaterSolvent3×HCID 6342AcetonitrileSolvent2×HCID 6344DichloromethaneSolvent

Procedure

First, in a recovery flask equipped with a reflux pipe were put 4.90 g of 4-chloro-6-methylpyrimidine, 4.80 g of phenylboronic acid, 4.03 g of sodium carbonate, 0.16 g of bis(triphenylphosphine)palladium(II) dichloride (abbreviation: Pd(PPh3)2Cl2), 20 mL of water, and 10 mL of acetonitrile, and the air in the flask was replaced with argon. This reaction container was subjected to irradiation with microwaves (2.45 GHz, 100W) for one hour to be heated. In the flask were further put 2.28 g of phenylboronic acid, 2.02 g of sodium carbonate, 0.082 g of Pd(PPh3)2Cl2, 5 mL of water, and 10 mL of acetonitrile, and the mixture was heated again by irradiation with microwaves (2.45 GHz, 100 W) for one hour. After that, water was added to this solution and extraction with dichloromethane was carried out. The obtained solution of the extract was washed with a saturated sodium carbonate aqueous solution, water, and then with saturated saline, and 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 dichloromethane and ethyl acetate as a developing solvent in a volume ratio of 9:1, so that a pyrimidine derivative Hmppm, which was a target substance, was obtained (orange oily substance, yield of 46%). Note that the irradiation with microwaves was performed with a microwave synthesis system (Discover, produced by CEM Corporation). The synthesis scheme of Step 1 is shown in (C-1).

Workup

  1. customFirst, in a recovery flask equipped with a reflux pipe
  2. temperatureto be heated
  3. temperaturethe mixture was heated again by irradiation with microwaves (2.45 GHz, 100 W) for one hour
  4. washThe obtained solution of the extract was washed with a saturated sodium carbonate aqueous solution, water
  5. dry with materialwith saturated saline, and 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. customwas obtained (orange oily substance, yield of 46%)
  11. customNote that the irradiation with microwaves
  12. customwas performed with a microwave synthesis system (Discover, produced by CEM Corporation)
  13. customThe synthesis scheme of Step 1

Sources & evidence

ORD record
ord-4cca15ec36684c788ca180f0cf90a6f9
Source dataset
uspto-grants-2015_07
Patent number
US09083000B2

Reaction notes

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