Diethyl 2-(p-tolyl)malonate → 5-(4-Methylphenyl)-4,6-dihydroxy-2-n-propylpyrimidine

HRID 2317Notes

Reaction equation

HRID 2317 reaction equation
C(O[C:4](=[O:18])[CH:5]([C:11]1[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][CH:12]=1)[C:6]([O:8]CC)=O)C.Cl.[C:20]([NH2:25])(=[NH:24])[CH2:21][CH2:22][CH3:23].C[O-].[Na+]>CO>[CH3:17][C:14]1[CH:13]=[CH:12][C:11]([C:5]2[C:4]([OH:18])=[N:24][C:20]([CH2:21][CH2:22][CH3:23])=[N:25][C:6]=2[OH:8])=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 570878Diethyl 2-(p-tolyl)malonateHCID 10942334Sodium MethoxideHCID 12828983Butanimidamide hydrochloride

Product 1

HCID 1784184665-(4-Methylphenyl)-4,6-dihydroxy-2-n-propylpyrimidineYield 56.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of diethyl(4-methylphenyl)malonate (9.45 g) and butyramidine hydrochloride (5.00 g) in methanol (25 ml) is added 28% sodium methoxide (19.67 g) under ice-cooling, and the mixture is stirred at room temperature overnight. After the reaction is complete, the reaction solution is concentrated to the half volume thereof, and the resultant is diluted with water. The mixture is acidified with 10% hydrochloric acid, and the precipitated crystals are collected by filtration, washed, and dried to give 5-(4-methylphenyl)-4,6-dihydroxy-2-n-propylpyrimidine (5.17 g) as crystalline powder.

Workup

  1. temperaturecooling
  2. concentrationthe reaction solution is concentrated to the half volume
  3. additionthe resultant is diluted with water
  4. filtrationthe precipitated crystals are collected by filtration
  5. washwashed
  6. customdried

Sources & evidence

ORD record
ord-fcdab10bc84144e59957a7d86566aed7
Source dataset
uspto-grants-1998_03
Patent number
US05728706

Reaction notes

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