2-Nitroamino-5-(6-methoxy-3-pyridylmethyl)-4-pyrimidone → 2-[2-(2-Thiazolylmethylthio)ethylamino]-5-(6-methoxy-3-pyridylmethyl)-4-pyrimidone

HRID 127199Notes

Reaction equation

HRID 127199 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.[S:21]1[CH:25]=[CH:24][N:23]=[C:22]1[CH2:26][S:27][CH2:28][CH2:29]N>C(O)C>[S:21]1[CH:25]=[CH:24][N:23]=[C:22]1[CH2:26][S:27][CH2:28][CH2:29][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 127838322-Nitroamino-5-(6-methoxy-3-pyridylmethyl)-4-pyrimidoneHCID 129234032-[(Thiazol-2-yl)methylthio]ethylamine

Product 1

HCID 127995592-[2-(2-Thiazolylmethylthio)ethylamino]-5-(6-methoxy-3-pyridylmethyl)-4-pyrimidoneYield 60%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

An equimolar mixture of 2-nitroamino-5-(6-methoxy-3-pyridylmethyl)-4-pyrimidone and 2-(2-thiazolylmethylthio) ethylamine was refluxed in ethanol for 18 hours. The solid which crystallised out on cooling was recrystallised from ethanol to give 2-[2-(2-thiazolylmethylthio)ethylamino]-5-(6-methoxy-3-pyridylmethyl)-4-pyrimidone, m.p. 95-97° in 60% yield.

Workup

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

Sources & evidence

ORD record
ord-815197395e3d48b4a3ca0850cebfe96f
Source dataset
uspto-grants-1981_03
Patent number
US04255428

Reaction notes

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