2-Nitroamino-5-(2-methoxy-4-pyridyl)methyl-4-pyrimidone → 2-[2-(2-Thiazolylmethylthio)ethylamino]-5-(2-methoxy-4-pyridylmethyl)-4-pyrimidone

HRID 127204Notes

Reaction equation

HRID 127204 reaction equation
[N+]([NH:4][C:5]1[NH:10][C:9](=[O:11])[C:8]([CH2:12][C:13]2[CH:18]=[CH:17][N:16]=[C:15]([O:19][CH3:20])[CH:14]=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:18]=[CH:17][N:16]=[C:15]([O:19][CH3:20])[CH:14]=2)=[CH:7][N:6]=1

Participants

4

Reactant 2

HCID 127838332-Nitroamino-5-(2-methoxy-4-pyridyl)methyl-4-pyrimidoneHCID 129234032-[(Thiazol-2-yl)methylthio]ethylamine

Product 1

HCID 127886732-[2-(2-Thiazolylmethylthio)ethylamino]-5-(2-methoxy-4-pyridylmethyl)-4-pyrimidoneYield 41%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

An equimolar mixture of 2-nitroamino-5-(2-methoxy-4-pyridylmethyl)-4-pyrimidone and 2-(2-thiazolylmethylthio) ethylamine was heated under reflux in ethanol for 18 hours. The solid which crystallised out on cooling was purified by column chromatography on silica gel and recrystallisation from 2-propanol-ethanol to give 2-[2-(2-thiazolylmethylthio)ethylamino]-5-(2-methoxy-4-pyridylmethyl)-4-pyrimidone, m.p. 105.5-106.5° in 41% yield. The latter compound was heated under reflux in 2N hydrogen chloride in ethanol for 24 hours to give 2-[2-(2-thiazolylmethylthio)ethylamino]-5-(2-hydroxy-4-pyridylmethyl)-4-pyrimidone monohydrochloride, m.p. 169-173°.

Workup

  1. temperaturewas heated
  2. customThe solid which crystallised out
  3. temperatureon cooling
  4. customwas purified by column chromatography on silica gel and recrystallisation from 2-propanol-ethanol

Sources & evidence

ORD record
ord-56db9e6533094204b55d3a919c30f6ab
Source dataset
uspto-grants-1981_03
Patent number
US04255428

Reaction notes

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