5-(3-Methoxybenzyl)-2-methylthio-4-pyrimidone → 2-[4-(5-Bromo-3-methylpyrid-2-yl)butylamino]-5-(3-methoxybenzyl)-4-pyrimidone

HRID 485660Notes

Reaction equation

HRID 485660 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH3:13])[C:5]([CH2:8][CH2:9][CH2:10][CH2:11][NH2:12])=[N:6][CH:7]=1.[CH3:14][O:15][C:16]1[CH:17]=[C:18]([CH:29]=[CH:30][CH:31]=1)[CH2:19][C:20]1[C:21](=[O:28])[NH:22][C:23](SC)=[N:24][CH:25]=1>N1C=CC=CC=1>[Br:1][C:2]1[CH:3]=[C:4]([CH3:13])[C:5]([CH2:8][CH2:9][CH2:10][CH2:11][NH:12][C:23]2[NH:22][C:21](=[O:28])[C:20]([CH2:19][C:18]3[CH:29]=[CH:30][CH:31]=[C:16]([O:15][CH3:14])[CH:17]=3)=[CH:25][N:24]=2)=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 129515265-(3-Methoxybenzyl)-2-methylthio-4-pyrimidoneHCID 130942724-(5-Bromo-3-methyl-2-pyridinyl)butylamine

Product 1

HCID 202690702-[4-(5-Bromo-3-methylpyrid-2-yl)butylamino]-5-(3-methoxybenzyl)-4-pyrimidoneYield 67.5%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

5-Bromo-2-(4-aminobutyl)-3-methylpyridine, (0.58 g) and 5-(3-methoxybenzyl)-2-methylthio-4-pyrimidone (0.51 g) were refluxed in pyridine (3 ml) for 3 hours. The pyridine was removed in vacuo. The residue was recrystallised from ethanol/water giving 2-[4-(5-bromo-3-methylpyrid-2-yl)butylamino]-5-(3-methoxybenzyl)-4-pyrimidone (0.60 g). Softens 65° C., melts 73° C.

Workup

  1. customThe pyridine was removed in vacuo
  2. customThe residue was recrystallised from ethanol/water

Sources & evidence

ORD record
ord-2dbcfc037ec942309b5e2f15fb2948ff
Source dataset
uspto-grants-1985_08
Patent number
US04537891

Reaction notes

Loading…