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

HRID 1674127Notes

Reaction equation

HRID 1674127 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-ae65ecd186a84f9995ac4e48b4039047
Source dataset
uspto-grants-2011_08
Patent number
US07998968B2

Reaction notes

Loading…