Ethyl Acetoacetate → 2-Butyl-6-methyl-4-pyrimidinol

HRID 2372841Notes

Reaction equation

HRID 2372841 reaction equation
Cl.[C:2]([NH2:8])(=[NH:7])[CH2:3][CH2:4][CH2:5][CH3:6].[C:9](OCC)(=[O:14])[CH2:10][C:11]([CH3:13])=O.C[O-].[Na+]>CO.[Cl-].[Na+].O.O>[CH2:3]([C:2]1[NH:8][C:9](=[O:14])[CH:10]=[C:11]([CH3:13])[N:7]=1)[CH2:4][CH2:5][CH3:6]

Participants

7

Reactant 3

HCID 8868Ethyl AcetoacetateHCID 10942334Sodium MethoxideHCID 11615174Pentanimidamide Hydrochloride

Product 1

HCID 1354243772-Butyl-6-methyl-4-pyrimidinol

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

A solution of 2.0 g valeramidine hydrochloride, 1.9 g ethyl acetoacetate, and 791 mg sodium methoxide in 20 mL methanol was refluxed for 24 hours. The mixture was diluted with brine and water and was extracted three times with ether. The combined organic material was washed with brine, was dried over MgSO4, was stripped of solvent in vacuo, and then was Still flash chromatographed in 4% MeOH in CH2Cl2 to give the title compound as a white solid 1H NMR (250 MHz, CDCl3) δ13.01 (br s, 1H), 6.18 (s, 1H), 2.67 (3 line m, 2H), 2.31 (s, 3H), 1.76 (m, 2H), 1.42 (m, 2H), 0.95 (3 line m, 3H).

Workup

  1. extractionwas extracted three times with ether
  2. washThe combined organic material was washed with brine
  3. dry with materialwas dried over MgSO4
  4. customchromatographed in 4% MeOH in CH2Cl2

Sources & evidence

ORD record
ord-1dff29c17e5c4f90a96f7e7b300d66d0
Source dataset
uspto-grants-1992_03
Patent number
US05100897

Reaction notes

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