2-[(Thiazol-2-yl)methylthio]ethylamine → 2-[2-(2-Thiazolylmethylthio)ethylamino]-5-(3-methoxybenzyl)-4-pyrimidone

HRID 903378Notes

Reaction equation

HRID 903378 reaction equation
[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[CH2:6][S:7][CH2:8][CH2:9][NH2:10].[N+](N[C:15]1[NH:20][C:19](=[O:21])[C:18]([CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([O:29][CH3:30])[CH:24]=2)=[CH:17][N:16]=1)([O-])=O>>[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[CH2:6][S:7][CH2:8][CH2:9][NH:10][C:15]1[NH:20][C:19](=[O:21])[C:18]([CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([O:29][CH3:30])[CH:24]=2)=[CH:17][N:16]=1

Participants

3

Reactant 2

HCID 129234032-[(Thiazol-2-yl)methylthio]ethylamineHCID 202792742-Nitroamino-5-(3-methoxybenzyl)-4-pyrimidone

Product 1

HCID 129515562-[2-(2-Thiazolylmethylthio)ethylamino]-5-(3-methoxybenzyl)-4-pyrimidoneYield 41.9%

Procedure

2-(2-Thiazolylmethylthio)ethylamine (2.00 g) and 2-nitroamino-5-(3-methoxybenzyl)-4-pyrimidone (1.58 g) were fused together at 130° for 4 hours. The mixture was triturated with hot water and the residue was recrystallised from 2-propanol to give 2-[2-(2-thiazolylmethylthio)ethylamino]-5-(3-methoxybenzyl)-4-pyrimidone (0.93 g), m.p. 122°-4°. A sample was treated with hydrogen chloride in ethanol and after recrystallision from isopropanol/methanol it had m.p. 104°-6° and gave analytical data corresponding to a hemihydrochloride.

Workup

  1. customThe mixture was triturated with hot water
  2. customthe residue was recrystallised from 2-propanol

Sources & evidence

ORD record
ord-90b144ecc7984649ad945ae98998f377
Source dataset
uspto-grants-1980_10
Patent number
US04227000

Reaction notes

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