Sodium Methoxide → Pyrimidine, 2-(6-bromo-2-pyridinyl)-4-methyl-

HRID 1651041Notes

Reaction equation

HRID 1651041 reaction equation
Cl.[Br:2][C:3]1[N:8]=[C:7]([C:9]([NH2:11])=[NH:10])[CH:6]=[CH:5][CH:4]=1.C[O-].[Na+]>CO.COC(OC)CC(=O)C>[Br:2][C:3]1[N:8]=[C:7]([C:9]2[N:11]=[C:5]([CH3:6])[CH:4]=[CH:3][N:10]=2)[CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 2

HCID 10942334Sodium MethoxideHCID 230513786-BroMopicoliniMidaMide hydrochloride

Product 1

HCID 11021289Pyrimidine, 2-(6-bromo-2-pyridinyl)-4-methyl-Yield 168.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 2285484,4-Dimethoxy-2-butanoneSolvent

Procedure

To a mixture of 6-bromo-2-picoline amidine hydrochloride (10 g) and methanol (200 ml) were added 28% sodium methoxide solution in methanol (10.6 g) and 1,1-dimethoxy-3-butanone (6.1 g). The mixture was heated under refluxing for an hour, and then concentrated under reduced pressure. Water (100 ml) and ethylacetate (200 ml) were added thereto, and then extracted. After the extract was dried over anhydrous magnesium sulfate, it was concentrated under reduced pressure. The residue was washed with n-hexane to obtain 2-(6-bromo-2-pyridinyl)-4-methylpyrimidine (8.9 g, yield 84%).

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder refluxing for an hour
  3. concentrationconcentrated under reduced pressure
  4. additionWater (100 ml) and ethylacetate (200 ml) were added
  5. extractionextracted
  6. dry with materialAfter the extract was dried over anhydrous magnesium sulfate, it
  7. concentrationwas concentrated under reduced pressure
  8. washThe residue was washed with n-hexane

Sources & evidence

ORD record
ord-101224141eff419787a9beb4f61385a6
Source dataset
uspto-grants-1990_05
Patent number
US04927827

Reaction notes

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