5-(4-Chlorobenzyl)-2-methylthiopyrimid-4-one → 2-[4-(3-Methyl-5-bromopyrid-2-yl)butylamino]-5-(4-chlorobenzyl)-4-pyrimidone

HRID 485655Notes

Reaction equation

HRID 485655 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.CS[C:16]1[NH:21][C:20](=[O:22])[C:19]([CH2:23][C:24]2[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][CH:25]=2)=[CH:18][N:17]=1>>[CH3:13][C:4]1[C:5]([CH2:8][CH2:9][CH2:10][CH2:11][NH:12][C:16]2[NH:21][C:20](=[O:22])[C:19]([CH2:23][C:24]3[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][CH:25]=3)=[CH:18][N:17]=2)=[N:6][CH:7]=[C:2]([Br:1])[CH:3]=1

Participants

3

Reactant 2

HCID 129459805-(4-Chlorobenzyl)-2-methylthiopyrimid-4-oneHCID 130942724-(5-Bromo-3-methyl-2-pyridinyl)butylamine

Product 1

HCID 202690692-[4-(3-Methyl-5-bromopyrid-2-yl)butylamino]-5-(4-chlorobenzyl)-4-pyrimidoneYield 77%

Procedure

5-Bromo-2-(4-aminobutyl)-3-methylpyridine, (0.73 g), was fused with 2-methylthio-5-(4-chlorobenzyl)-4-pyrimidone (0.75 g) at 160°-170° C. and heating was continued for 6 hours. The mixture was cooled and recrystallised from chloroform/petroleum-ether (b.p. 60°-80° C.), to give 2-[4-(3-methyl-5-bromopyrid-2-yl)butylamino]-5-(4-chlorobenzyl)-4-pyrimidone (1.0 g) m.p. 149°-150° C.

Workup

  1. temperatureheating
  2. temperatureThe mixture was cooled
  3. customrecrystallised from chloroform/petroleum-ether (b.p. 60°-80° C.)

Sources & evidence

ORD record
ord-a6b5726fc52e460098347b1f1d0c6842
Source dataset
uspto-grants-1985_08
Patent number
US04537891

Reaction notes

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