Sodium ethoxide → 2-[2-(2-Thienylmethylthio)ethylamino]-5-(3-pyridylmethyl)-4-pyrimidone

HRID 1719147Notes

Reaction equation

HRID 1719147 reaction equation
Cl.[S:2]1[CH:6]=[CH:5][CH:4]=[C:3]1[CH2:7][S:8][CH2:9][CH2:10][NH2:11].[O-]CC.[Na+].[N+](N[C:20]1[NH:25][C:24](=[O:26])[C:23]([CH2:27][C:28]2[CH:29]=[N:30][CH:31]=[CH:32][CH:33]=2)=[CH:22][N:21]=1)([O-])=O>C(O)C>[S:2]1[CH:6]=[CH:5][CH:4]=[C:3]1[CH2:7][S:8][CH2:9][CH2:10][NH:11][C:20]1[NH:25][C:24](=[O:26])[C:23]([CH2:27][C:28]2[CH:29]=[N:30][CH:31]=[CH:32][CH:33]=2)=[CH:22][N:21]=1

Participants

5

Reactant 3

HCID 2723922Sodium ethoxideHCID 12788688N-{6-Oxo-5-[(pyridin-3-yl)methyl]-1,6-dihydropyrimidin-2-yl}nitramideHCID 135053102-(2-Thienylmethylthio)ethylamine hydrochloride

Product 1

HCID 135052962-[2-(2-Thienylmethylthio)ethylamino]-5-(3-pyridylmethyl)-4-pyrimidone

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

2-(2-Thienylmethylthio)ethylamine hydrochloride (2 g) in ethanol (25 ml) was added to a solution of sodium ethoxide (prepared from 0.218 g sodium) in ethanol and the mixture was stirred for 0.5 hour. 2-Nitroamino-5-(3-pyridylmethyl)-4-pyrimidone (2.34 g) was added and the mixture was boiled under reflux for 40 hours and evaporated to dryness. Pyridine (50 ml) was added to the residue and the mixture was boiled under reflux for 24 hours and evaporated. The residue was crystallised from ethanol/ethyl acetate and further purified by elution from a column of silica gel with ethyl acetate/methanol (5.1) and recrystallisation from 2-propanol to give 2-[2-(2-thienylmethylthio)ethylamino]-5-(3-pyridylmethyl)-4-pyrimidone m.p. 145°-148°.

Workup

  1. temperatureunder reflux for 40 hours
  2. customevaporated to dryness
  3. additionPyridine (50 ml) was added to the residue
  4. temperatureunder reflux for 24 hours
  5. customevaporated
  6. customThe residue was crystallised from ethanol/ethyl acetate
  7. customfurther purified by elution from a column of silica gel with ethyl acetate/methanol (5.1) and recrystallisation from 2-propanol

Sources & evidence

ORD record
ord-fd4d128f087b48c6a162290efccaca34
Source dataset
uspto-grants-1985_09
Patent number
US04539207

Reaction notes

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