Sodium Hydroxide → HCID 20430499, compound

HRID 2413166Notes

Reaction equation

HRID 2413166 reaction equation
Cl.Cl.[CH3:3][N:4]([CH2:6][C:7]1[CH:8]=[C:9]([CH:15]=[CH:16][CH:17]=1)[CH2:10][S:11][CH2:12][CH2:13][NH2:14])[CH3:5].[OH-].[Na+].[N+](N[C:24]1[NH:29][C:28](=[O:30])[C:27]([CH2:31][C:32]2[CH:33]=[N:34][CH:35]=[CH:36][CH:37]=2)=[CH:26][N:25]=1)([O-])=O>O.C(O)C>[CH3:5][N:4]([CH2:6][C:7]1[CH:8]=[C:9]([CH:15]=[CH:16][CH:17]=1)[CH2:10][S:11][CH2:12][CH2:13][NH:14][C:24]1[NH:29][C:28](=[O:30])[C:27]([CH2:31][C:32]2[CH:33]=[N:34][CH:35]=[CH:36][CH:37]=2)=[CH:26][N:25]=1)[CH3:3]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 12788688N-{6-Oxo-5-[(pyridin-3-yl)methyl]-1,6-dihydropyrimidin-2-yl}nitramideHCID 20430490HCID 20430490, compound

Product 1

HCID 20430499HCID 20430499, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

2-[3-(Dimethylaminomethyl)benzylthio]ethylamine dihydrochloride (4.2 g) was dissolved in water and the solution was made alkaline with aqueous sodium hydroxide and extracted with chloroform. The chloroform extract was evaporated to give the free base. 2-Nitroamino-5-(3-pyridylmethyl)-4-pyrimidone (3.16 g) was added to the residue and the mixture was heated under reflux in ethanol (20 ml) for 35 hours and evaporated to dryness. Water (30 ml) was added to the residue and the mixture was adjusted to pH 13 with aqueous sodium hydroxide and extracted with chloroform. The latter chloroform extracts were evaporated and the residue was recrystallised from acetonitrile to give 2-[2-(3-(dimethylaminomethyl)-benzylthio)ethylamino]-5-(3-pyridylmethyl)-4-pyrimidone m.p. 143°-145°. Treatment with hydrogen chloride in ethanol gives the trihydrochloride salt and treatment with hydrogen bromide in ethanol gives the trihydrobromide salt.

Workup

  1. extractionextracted with chloroform
  2. extractionThe chloroform extract
  3. customwas evaporated
  4. customto give the free base
  5. temperaturethe mixture was heated
  6. customevaporated to dryness
  7. additionWater (30 ml) was added to the residue
  8. extractionextracted with chloroform
  9. customThe latter chloroform extracts were evaporated
  10. customthe residue was recrystallised from acetonitrile

Sources & evidence

ORD record
ord-a852f62d7d3d485daac175b685e235c4
Source dataset
uspto-grants-1985_01
Patent number
US04496567

Reaction notes

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