4-(((2-Aminoethyl)thio)methyl)-5-methylimidazole → HCID 3054539, compound

HRID 1855840Notes

Reaction equation

HRID 1855840 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][C:7]1[C:8](=[O:15])[NH:9][C:10](SC)=[N:11][CH:12]=1.[CH3:16][C:17]1[NH:21][CH:20]=[N:19][C:18]=1[CH2:22][S:23][CH2:24][CH2:25][NH2:26]>>[CH3:16][C:17]1[NH:21][CH:20]=[N:19][C:18]=1[CH2:22][S:23][CH2:24][CH2:25][NH:26][C:10]1[NH:9][C:8](=[O:15])[C:7]([CH2:6][C:2]2[S:1][CH:5]=[CH:4][CH:3]=2)=[CH:12][N:11]=1

Participants

3

Reactant 2

HCID 6655684-(((2-Aminoethyl)thio)methyl)-5-methylimidazoleHCID 14338588HCID 14338588, compound

Product 1

HCID 3054539HCID 3054539, compound

Procedure

An intimate mixture of 5-(2-thienylmethyl)-2-methylthio-4-pyrimidone (1.43 g) and 2-(5-methyl-4-imidazolylmethylthio)ethylamine (1.03 g) was heated at 140° for 6 hours. The cooled residue was washed with water to give 2-[2-(5-methyl-4-imidazolylmethylthio)ethylamino]-5-(2-thienylmethyl)-4-pyrimidone, and this product was treated with dilute ethanolic HCl to give the title compound in 40% yield, m.p. 172°-176° (ethanol-acetonitrile). The dihydrochloride was passed down an ion-exchange column of IRA 400 eluting with 1 N hydrobromic acid, and the eluate was evaporated to dryness and recrystallised from ethanol acetonitrile to give the corresponding dihydrobromide m.p. 99°-203°. (Found: C, 36.7; H, 4.2; N, 13.5; S, 12.1; Br, 30.6; C16H19N5OS2.2HBr Requires: C, 36.7; H, 4.0; N, 13.4; S, 12.2; Br, 30.5%)

Workup

  1. temperaturewas heated at 140° for 6 hours
  2. washThe cooled residue was washed with water

Sources & evidence

ORD record
ord-68f1443195034cf394a52a56ad2544b4
Source dataset
uspto-grants-1980_08
Patent number
US04216318

Reaction notes

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