2-Methylthio-5-(3,4-methylenedioxybenzyl)pyrimid-4-one → 2-[4-(5-Bromo-3-methylpyrid-2-yl)butylamino]-5-(3,4-methylenedioxybenzyl)-4-pyrimidone

HRID 485661Notes

Reaction equation

HRID 485661 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.[CH2:14]1[O:32][C:31]2[CH:30]=[CH:29][C:18]([CH2:19][C:20]3[C:21](=[O:28])[NH:22][C:23](SC)=[N:24][CH:25]=3)=[CH:17][C:16]=2[O:15]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:31]4[O:32][CH2:14][O:15][C:16]=4[CH:17]=3)=[CH:25][N:24]=2)=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 129451572-Methylthio-5-(3,4-methylenedioxybenzyl)pyrimid-4-oneHCID 130942724-(5-Bromo-3-methyl-2-pyridinyl)butylamine

Product 1

HCID 202690742-[4-(5-Bromo-3-methylpyrid-2-yl)butylamino]-5-(3,4-methylenedioxybenzyl)-4-pyrimidoneYield 77.7%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

5-Bromo-2-(4-aminobutyl)-3-methylpyridine, (0.88 g) and 5-(3,4-methylenedioxybenzyl)-2-methylthio-4-pyrimidone (0.83 g) were refluxed in pyridine (3 ml) for 24 hours. The pyridine was removed in vacuo and the resulting brown oil triturated with ethanol giving a cream solid which was recrystallised from dimethylformamide/ethanol giving 2-[4-(5-bromo-3-methylpyrid-2-yl)butylamino]-5-(3,4-methylenedioxybenzyl)-4-pyrimidone (1.1 g) as a colourless solid m.p. 145°-6° C.

Workup

  1. customThe pyridine was removed in vacuo
  2. customthe resulting brown oil triturated with ethanol giving a cream solid which
  3. customwas recrystallised from dimethylformamide/ethanol

Sources & evidence

ORD record
ord-8a33d77d54b346b88ea3a72b999af3ba
Source dataset
uspto-grants-1985_08
Patent number
US04537891

Reaction notes

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