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

HRID 224856Notes

Reaction equation

HRID 224856 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][CH:16]=[CH:17][CH:18]=2)=[CH:7][N:6]=1)([O-])=O.Cl.[O:20]1[C:24]([CH2:25][S:26][CH2:27][CH2:28]N)=[CH:23][CH:22]=[CH:21]1.[O-]CC.[Na+]>C(O)C>[O:20]1[CH:21]=[CH:22][CH:23]=[C:24]1[CH2:25][S:26][CH2:27][CH2:28][NH:4][C:5]1[NH:10][C:9](=[O:11])[C:8]([CH2:12][C:13]2[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=2)=[CH:7][N:6]=1

Participants

5

Reactant 3

HCID 2723922Sodium ethoxideHCID 12788688N-{6-Oxo-5-[(pyridin-3-yl)methyl]-1,6-dihydropyrimidin-2-yl}nitramideHCID 202133192-(5-Furylmethylthio)ethylamine hydrochloride

Product 1

HCID 135052952-[2-(2-Furylmethylthio)ethylamino]-5-(3-pyridylmethyl)-4-pyrimidone

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(b)(i) 2-Nitroamino-5-(3-pyridylmethyl)-4-pyrimidone (12.36 g) was added to a stirred mixture of 2-(5-furylmethylthio)ethylamine hydrochloride (10.65 g) and sodium ethoxide (prepared from 1.26 g sodium) in dry ethanol (300 ml) and the mixture was boiled under reflux for 44 hours and evaporated to dryness. The residue was triturated with water (discarded) and recrystallised from aqueous 2-propanol to give 2-[2-(2-furylmethylthio)ethylamino]-5-(3-pyridylmethyl)-4-pyrimidone, m.p. 136°-139°.

Workup

  1. temperatureunder reflux for 44 hours
  2. customevaporated to dryness
  3. customThe residue was triturated with water (discarded)
  4. customrecrystallised from aqueous 2-propanol

Sources & evidence

ORD record
ord-19b976957ad9426fb8b7ff4d0bfb2a8f
Source dataset
uspto-grants-1980_11
Patent number
US04234588

Reaction notes

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