Methanol → 4-Methyl-6-(1-methylethyl)pyrimidine

HRID 491271Notes

Reaction equation

HRID 491271 reaction equation
Cl[C:2]1[C:7](C(C)C)=[C:6]([CH3:11])[N:5]=[CH:4][N:3]=1.[C:12]([O-])(=O)[CH3:13].[Na+].[CH3:17]O>[Pd]>[CH3:11][C:6]1[CH:7]=[C:2]([CH:12]([CH3:13])[CH3:17])[N:3]=[CH:4][N:5]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 517045Sodium AcetateHCID 629159014-Chloro-6-methyl-5-(propan-2-yl)pyrimidine

Product 1

HCID 536494874-Methyl-6-(1-methylethyl)pyrimidineYield 81%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

4-Chloro-5-isopropyl-6-methylpyrimidine (5.0 g, 29 mmol) and sodium acetate (3.1 g, 38 mmol) were combined in 75 ml methanol and hydrogenated over 500 mg 5 percent palladium on carbon for 20 h. After removal of the catalyst by filtration, the solvent was removed by evaporation. The residue was treated with sat. sodium bicarbonate solution and extracted with diethyl ether. The ether extracts were washed with sat. brine, dried (Na2SO4) and evaporated to give 3.2 g (81 percent yield).

Workup

  1. customAfter removal of the catalyst
  2. filtrationby filtration
  3. customthe solvent was removed by evaporation
  4. additionThe residue was treated with sat. sodium bicarbonate solution
  5. extractionextracted with diethyl ether
  6. washThe ether extracts were washed with sat. brine
  7. dry with materialdried (Na2SO4)
  8. customevaporated
  9. customto give 3.2 g (81 percent yield)

Sources & evidence

ORD record
ord-c5914be169c54000a4c1bcc471f555a3
Source dataset
uspto-grants-2009_05
Patent number
US07531482B2

Reaction notes

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