2-{[(3-Bromopyridin-2-yl)methyl]sulfanyl}ethan-1-amine → 4(1H)-Pyrimidinone, 2-((2-(((3-bromo-2-pyridinyl)methyl)thio)ethyl)amino)-5-(2-pyridinylmethyl)-, trihydrobromide

HRID 1855845Notes

Reaction equation

HRID 1855845 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][C:8]1[C:9](=[O:16])[NH:10][C:11](SC)=[N:12][CH:13]=1.[Br:17][C:18]1[C:19]([CH2:24][S:25][CH2:26][CH2:27][NH2:28])=[N:20][CH:21]=[CH:22][CH:23]=1>>[BrH:17].[BrH:17].[BrH:17].[Br:17][C:18]1[C:19]([CH2:24][S:25][CH2:26][CH2:27][NH:28][C:11]2[NH:10][C:9](=[O:16])[C:8]([CH2:7][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=3)=[CH:13][N:12]=2)=[N:20][CH:21]=[CH:22][CH:23]=1

Participants

3

Reactant 2

HCID 129515272-{[(3-Bromopyridin-2-yl)methyl]sulfanyl}ethan-1-amineHCID 14338586HCID 14338586, compound

Product 1

HCID 30489094(1H)-Pyrimidinone, 2-((2-(((3-bromo-2-pyridinyl)methyl)thio)ethyl)amino)-5-(2-pyridinylmethyl)-, trihydrobromideYield 44.5%

Procedure

An intimate mixture of 5-(2-pyridylmethyl)-2-methylthio-4-pyrimidone (1.5 g) and 2-(3-bromo-2-pyridylmethythio)-ethylamine (1.6 g) was heated at 130° for 6 hours. After cooling, the residue was triturated with hot water and treated with dilute hydrobromic acid to give the title compound, in 44.5% yield, m.p. 225°-230° (decomp.) (ex methanol-water).

Workup

  1. temperaturewas heated at 130° for 6 hours
  2. temperatureAfter cooling
  3. customthe residue was triturated with hot water
  4. additiontreated with dilute hydrobromic acid

Sources & evidence

ORD record
ord-071d255e55e5446daf7bea04a56a4447
Source dataset
uspto-grants-1980_08
Patent number
US04216318

Reaction notes

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