Butanimidamide hydrochloride → 5-(3-acetylbenzyl)-6-methyl-2-propylpyrimidin-4(3H)-one

HRID 1673606Notes

Reaction equation

HRID 1673606 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([CH:17]=[CH:18][CH:19]=1)[CH2:7][CH:8]([C:14](=O)[CH3:15])[C:9]([O:11]CC)=O)(=[O:3])[CH3:2].Cl.[C:21](=[NH:26])([NH2:25])[CH2:22][CH2:23][CH3:24].C[O-].[Na+].CO>CO>[C:1]([C:4]1[CH:5]=[C:6]([CH:17]=[CH:18][CH:19]=1)[CH2:7][C:8]1[C:9](=[O:11])[NH:26][C:21]([CH2:22][CH2:23][CH3:24])=[N:25][C:14]=1[CH3:15])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 12828983Butanimidamide hydrochlorideHCID 23694274Sodium methanolate methanolHCID 57460081Ethyl 2-(3-acetylbenzyl)-3-oxobutanoate

Product 1

HCID 1360267485-(3-acetylbenzyl)-6-methyl-2-propylpyrimidin-4(3H)-oneYield 78%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of ethyl 2-(3-acetylbenzyl)-3-oxobutanoate (2.39 g) and butanimidamide hydrochloride (1.68 g) in methanol (20 mL) was added 28% sodium methoxide-methanol solution (5.27 mL), and the mixture was stirred for 12 hr. The reaction mixture was concentrated, and the residue was dissolved in water and diethyl ether. The aqueous layer was separated, and weakly acidified with 1 M hydrochloric acid. The precipitate was collected by filtration and dried under reduced pressure to give the title compound (2.02 g, 78%) as a colorless solid.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. dissolutionthe residue was dissolved in water
  3. customThe aqueous layer was separated
  4. filtrationThe precipitate was collected by filtration
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-af32973539e543f0ad66fe4b81986e4b
Source dataset
uspto-grants-2011_08
Patent number
US07998968B2

Reaction notes

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