Toluene → HCID 178494250, compound

HRID 653190Notes

Reaction equation

HRID 653190 reaction equation
[CH3:1][O-:2].[Na+].Cl[C:5]1[N:10]=[C:9]([O:11]CC2C=CC=CC=2)[C:8]([CH2:19][C:20]2[CH:21]=[N:22][C:23]([CH3:26])=[CH:24][CH:25]=2)=[CH:7][N:6]=1.C1(C)C=CC=CC=1>CO>[CH3:1][O:2][C:5]1[NH:6][CH:7]=[C:8]([CH2:19][C:20]2[CH:21]=[N:22][C:23]([CH3:26])=[CH:24][CH:25]=2)[C:9](=[O:11])[N:10]=1

Participants

5

Reactant 3

HCID 1140TolueneHCID 10942334Sodium MethoxideHCID 13374347HCID 13374347, compound

Product 1

HCID 178494250HCID 178494250, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 13.25 ml (0.0581 m) of 25% sodium methoxide in methanol was added dropwise to a mixture of 20 g (0.063 m) of 2-chloro-4-benzyloxy-5-[(6-methyl-3-pyridinyl)-methyl]-pyrimidine prepared as in Example 3 and 250 ml of toluene. The mixture was allowed to stir overnight at room temperature then washed with water and evaporated. The residual oil which was 2-methoxy-4-benzyloxy-5-[(6-methyl-3-pyridinyl)-methyl]-pyrimidine was dissolved in ethanol and hydrogenated over 0.6 g of 10% palladium on charcoal. After hydrogen absorption, the reaction mixture was filtered, concentrated to an oil which was taken up in methylene dichloride. Ether was added to give 8.4 g (59%) of 2-methoxy-5-[(6-methyl-3-pyridinyl)-methyl]-4-(1H)-pyrimidinone, m.p. 145°-147°.

Workup

  1. washthen washed with water
  2. customevaporated
  3. dissolutionwas dissolved in ethanol
  4. customAfter hydrogen absorption
  5. filtrationthe reaction mixture was filtered
  6. concentrationconcentrated to an oil which
  7. additionEther was added

Sources & evidence

ORD record
ord-b97dfa9471e34bccb2370b541025dedf
Source dataset
uspto-grants-1987_06
Patent number
US04675406

Reaction notes

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