Triethylamine → 2-n-Butyl-5-ethyl-6-methylpyrimidin-4(3H)-one

HRID 1681937Notes

Reaction equation

HRID 1681937 reaction equation
Cl.[C:2]([NH2:8])(=[NH:7])[CH2:3][CH2:4][CH2:5][CH3:6].C([O:11][C:12](=O)[CH:13]([CH2:17][CH3:18])[C:14]([CH3:16])=O)C.C(N(CC)CC)C>CN(C=O)C.[Cl-].[Na+].O>[CH2:3]([C:2]1[NH:8][C:12](=[O:11])[C:13]([CH2:17][CH3:18])=[C:14]([CH3:16])[N:7]=1)[CH2:4][CH2:5][CH3:6]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 79065Butanoic acid, 2-ethyl-3-oxo-, ethyl esterHCID 11615174Pentanimidamide Hydrochloride

Product 1

HCID 1356254552-n-Butyl-5-ethyl-6-methylpyrimidin-4(3H)-one

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

A solution of 3.0 g valeramidine hydrochloride, 3.47 g ethyl-2 ethylacetoacetate, and 5.8 mL triethylamine in 20 mL DMF was heated to 120° C. for 18 hours. The mixture was diluted with brine and 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 3% MeOH in CH2Cl2 to give the title compound as a white solid.

Workup

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

Sources & evidence

ORD record
ord-81b68937ee88473d86b532b9d8e72a2f
Source dataset
uspto-grants-1992_12
Patent number
US05175164

Reaction notes

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