Ethyl Acetate → 2-butyl-5-(3,3-dimethyl-2-oxobutyl)-6-methylpyrimidin-4(3H)-one

HRID 1718797Notes

Reaction equation

HRID 1718797 reaction equation
[C:1]([CH:4]([CH2:10][C:11](=[O:16])[C:12]([CH3:15])([CH3:14])[CH3:13])[C:5]([O:7]CC)=O)(=O)[CH3:2].[C:17](=[NH:23])([NH2:22])[CH2:18][CH2:19][CH2:20][CH3:21].C[O-].[Na+].CO.C(OCC)(=O)C>CO.O>[CH2:18]([C:17]1[NH:23][C:5](=[O:7])[C:4]([CH2:10][C:11](=[O:16])[C:12]([CH3:13])([CH3:14])[CH3:15])=[C:1]([CH3:2])[N:22]=1)[CH2:19][CH2:20][CH3:21]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 4097830PentanimidamideHCID 11775940Ethyl 2-acetyl-5,5-dimethyl-4-oxohexanoateHCID 23694274Sodium methanolate methanol

Product 1

HCID 1361467962-butyl-5-(3,3-dimethyl-2-oxobutyl)-6-methylpyrimidin-4(3H)-one

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of ethyl 2-acetyl-5,5-dimethyl-4-oxohexanoate (1.04 g) and pentanimidamide (0.89 g) in methanol (10 mL) was added 28% sodium methoxide-methanol solution (3.7 mL), and the mixture was stirred at room temperature for 24 hr. Ethyl acetate and water were added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated and the residue was purified by silica gel column chromatography to give the title compound as a pale-yellow viscous substance (0.34 g, 36%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated
  5. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-a7426b9a7a39444c8cbcde0c4fc282fa
Source dataset
uspto-grants-2010_09
Patent number
US07803940B2

Reaction notes

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