5-((6-Methyl-3-pyridyl)methyl)-2-(nitroamino)-1H-pyrimidin-4-one → HCID 20430525, compound

HRID 2413171Notes

Reaction equation

HRID 2413171 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]([CH3:19])=[CH:17][CH:18]=2)=[CH:7][N:6]=1)([O-])=O.[CH3:20][N:21]([CH2:23][C:24]1[CH:25]=[C:26]([CH:32]=[CH:33][CH:34]=1)[CH2:27][S:28][CH2:29][CH2:30]N)[CH3:22]>C(O)C>[CH3:20][N:21]([CH2:23][C:24]1[CH:25]=[C:26]([CH:32]=[CH:33][CH:34]=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]([CH3:19])=[CH:17][CH:18]=2)=[CH:7][N:6]=1)[CH3:22]

Participants

4

Reactant 2

HCID 30183605-((6-Methyl-3-pyridyl)methyl)-2-(nitroamino)-1H-pyrimidin-4-oneHCID 129520192-[[3-(N,N-Dimethylaminomethyl)phenyl]methylthio]ethanamine

Product 1

HCID 20430525HCID 20430525, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-nitroamino-5-(6-methyl-3-pyridylmethyl)-4-pyrimidone (1.0 g),2-[3-(dimethylaminomethyl)benzylthio]ethylamine (1.30 g, 1.5 equivalents) and ethanol (3 ml) was heated under reflux for 29 hours and evaporated to dryness. The residue was dissolved in water and the solution was adjusted to pH13 and extracted with ether (which was discarded). The aqueous phase was adjusted to pH 10.5 with hydrochloric acid and the solution was extracted with ether and chloroform. The combined organic extracts were evaporated to dryness and the residue was crystallised from acetonitrile to give 2-[2-[3-(dimethylaminomethyl)benzylthio]ethylamino]-5-(6-methyl-3-pyridylmethyl)-4-pyrimidone m.p. 122°-125°. Treatment with hydrogen chloride in ethanol gives the trihydrochloride salt and treatment with hydrogen bromide in ethanol gives the trihydrobromide salt.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 29 hours
  3. customevaporated to dryness
  4. dissolutionThe residue was dissolved in water
  5. extractionextracted with ether (which was discarded)
  6. extractionthe solution was extracted with ether and chloroform
  7. customThe combined organic extracts were evaporated to dryness
  8. customthe residue was crystallised from acetonitrile

Sources & evidence

ORD record
ord-2d765ccb14264ccdb12f0d0a30ab4782
Source dataset
uspto-grants-1985_01
Patent number
US04496567

Reaction notes

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