4-(((2-Aminoethyl)thio)methyl)-5-methylimidazole → 2-[2-(5-Methyl-4-imidazolylmethylthio)ethylamino]-5-(6-methoxy-3-pyridylmethyl)-4-pyrimidone

HRID 903376Notes

Reaction equation

HRID 903376 reaction equation
[N+]([NH:4][C:5]1[NH:10][C:9](=[O:11])[C:8]([CH2:12][C:13]2[CH:14]=[N:15][C:16]([O:19][CH3:20])=[CH:17][CH:18]=2)=[CH:7][N:6]=1)([O-])=O.[CH3:21][C:22]1[NH:26][CH:25]=[N:24][C:23]=1[CH2:27][S:28][CH2:29][CH2:30]N>C(O)C>[CH3:21][C:22]1[NH:26][CH:25]=[N:24][C:23]=1[CH2:27][S:28][CH2:29][CH2:30][NH:4][C:5]1[NH:10][C:9](=[O:11])[C:8]([CH2:12][C:13]2[CH:14]=[N:15][C:16]([O:19][CH3:20])=[CH:17][CH:18]=2)=[CH:7][N:6]=1

Participants

4

Reactant 2

HCID 6655684-(((2-Aminoethyl)thio)methyl)-5-methylimidazoleHCID 127838322-Nitroamino-5-(6-methoxy-3-pyridylmethyl)-4-pyrimidone

Product 1

HCID 127886642-[2-(5-Methyl-4-imidazolylmethylthio)ethylamino]-5-(6-methoxy-3-pyridylmethyl)-4-pyrimidoneYield 63%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

An equimolar mixture of 2-nitroamino-5-(6-methoxy-3-pyridylmethyl)-4-pyrimidone and 2-(5-methyl-4-imidazolylmethylthio)-ethylamine was heated under reflux in ethanol for 18 hours. The solid which crystallised out on cooling was recrystallised from ethanol to give 2-[2-(5-methyl-4-imidazolylmethylthio)ethylamino]-5-(6-methoxy-3-pyridylmethyl)-4-pyrimidone, m.p. 197°-8.5°, in 63% yield.

Workup

  1. temperaturewas heated
  2. customThe solid which crystallised out
  3. temperatureon cooling
  4. customwas recrystallised from ethanol

Sources & evidence

ORD record
ord-b38788c30f154c069ebdd6554df1f16c
Source dataset
uspto-grants-1980_10
Patent number
US04227000

Reaction notes

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