4-(5-Bromo-3-methyl-2-pyridinyl)butylamine → 2-[4-(5-Bromo-3-methylpyrid-2-yl)butylamino]-5-(4-fluorobenzyl)-4-pyrimidone

HRID 485659Notes

Reaction equation

HRID 485659 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.[F:14][C:15]1[CH:30]=[CH:29][C:18]([CH2:19][C:20]2[C:21](=[O:28])[NH:22][C:23](SC)=[N:24][CH:25]=2)=[CH:17][CH:16]=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][C:15]([F:14])=[CH:16][CH:17]=3)=[CH:25][N:24]=2)=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 130942724-(5-Bromo-3-methyl-2-pyridinyl)butylamineHCID 202628785-(4-Fluorobenzyl)-2-methylthio-4-pyrimidone

Product 1

HCID 202690672-[4-(5-Bromo-3-methylpyrid-2-yl)butylamino]-5-(4-fluorobenzyl)-4-pyrimidoneYield 71.9%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

5-Bromo-2-(4-aminobutyl)-3-methylpyridine, (0.88 g) and 5-(4-fluorobenzyl)-2-methylthio-4-pyrimidone (0.75 g) were refluxed in pyridine (3 ml) for 24 hours. The pyridine was removed in vacuo and the residue triturated with ethanol (5 ml) giving a colourless solid. The solid was recrystallised from methanol giving 2-[4-(5-bromo-3-methylpyrid-2-yl)butylamino]-5-(4-fluorobenzyl)-4-pyrimidone (0.96 g) m.p. 172°-3° C.

Workup

  1. customThe pyridine was removed in vacuo
  2. customthe residue triturated with ethanol (5 ml)
  3. customgiving a colourless solid
  4. customThe solid was recrystallised from methanol

Sources & evidence

ORD record
ord-892375f0ccbc4479bbf2ee1991c12d71
Source dataset
uspto-grants-1985_08
Patent number
US04537891

Reaction notes

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