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

HRID 485658Notes

Reaction equation

HRID 485658 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:31]=[CH:30][C:19]([CH2:20][C:21]2[C:22](=[O:29])[NH:23][C:24](SC)=[N:25][CH:26]=2)=[CH:18][CH:17]=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:24]2[NH:23][C:22](=[O:29])[C:21]([CH2:20][C:19]3[CH:30]=[CH:31][C:16]([O:15][CH3:14])=[CH:17][CH:18]=3)=[CH:26][N:25]=2)=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 129515135-(4-Methoxybenzyl)-2-methylthio-4-pyrimidoneHCID 130942724-(5-Bromo-3-methyl-2-pyridinyl)butylamine

Product 1

HCID 202690722-[4-(5-Bromo-3-methylpyrid-2-yl)butylamino]-5-(4-methoxybenzyl)-4-pyrimidoneYield 70.8%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

5-Bromo-2-(4-aminobutyl)-3-methylpyridine, (0.875 g) and 5-(4-methoxybenzyl)-2-methylthio-4-pyrimidone (0.786 g) were refluxed in pyridine (3 ml) for 20 hours. The pyridine was evaporated in vacuo. Residual pyridine was removed from the residue by azeotroping with water in vacuo and dried by azeotroping with ethanol. Addition of water (10 ml) and ethanol (1 ml) gave a colourless solid. This was recrystallised from ethanol and then from methanol to give 2-[4-(5-bromo-3-methylpyrid-2-yl)butylamino]-5-(4-methoxybenzyl)-4-pyrimidone (0.97 g) m.p. 149°-50° C.

Workup

  1. customThe pyridine was evaporated in vacuo
  2. customResidual pyridine was removed from the residue
  3. customby azeotroping with water in vacuo
  4. customdried
  5. customby azeotroping with ethanol
  6. additionAddition of water (10 ml) and ethanol (1 ml)
  7. customgave a colourless solid
  8. customThis was recrystallised from ethanol

Sources & evidence

ORD record
ord-263410d0620444c3af3be7a672c33dbe
Source dataset
uspto-grants-1985_08
Patent number
US04537891

Reaction notes

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