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

HRID 2372840Notes

Reaction equation

HRID 2372840 reaction equation
Cl.[C:2]([NH2:8])(=[NH:7])[CH2:3][CH2:4][CH2:5][CH3:6].[CH2:9]([CH:11]([C:17]([CH3:19])=O)[C:12](OCC)=[O:13])[CH3:10].C(N(CC)CC)C>CN(C=O)C.[Cl-].[Na+].O>[CH2:3]([C:2]1[NH:8][C:12](=[O:13])[C:11]([CH2:17][CH3:19])=[C:9]([CH3:10])[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. 1H NMR (300 MHz, CDCl3) δ2.62 (3 line m, 2H), 2.51 (4 line m, 2H), 2.32 (s, 3H), 1.75 (m, 2H), 1.42 (6 line m, 2H), 1.10 (3 line m, 3H), 0.95 (3 line m, 3H).

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-035186481efd4c73b46ecfdb0bf7a8d6
Source dataset
uspto-grants-1992_03
Patent number
US05100897

Reaction notes

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