3-Pyridylmethyl-2-methylthio-4-pyrimidone → HCID 20430551, compound

HRID 2413156Notes

Reaction equation

HRID 2413156 reaction equation
[CH3:1][O:2][C:3]1[CH:13]=[CH:12][CH:11]=[CH:10][C:4]=1[CH2:5][S:6][CH2:7][CH2:8][NH2:9].CS[C:16]1[NH:21][C:20](=[O:22])[C:19]([CH2:23][C:24]2[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=2)=[CH:18][N:17]=1>O>[CH3:1][O:2][C:3]1[CH:13]=[CH:12][CH:11]=[CH:10][C:4]=1[CH2:5][S:6][CH2:7][CH2:8][NH:9][C:16]1[NH:21][C:20](=[O:22])[C:19]([CH2:23][C:24]2[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=2)=[CH:18][N:17]=1

Participants

4

Reactant 2

HCID 127838233-Pyridylmethyl-2-methylthio-4-pyrimidoneHCID 20430498HCID 20430498, compound

Product 1

HCID 20430551HCID 20430551, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2-(2-Methoxybenzylthio)ethylamine (1.18 g) and 2-methylthio-5-(3-pyridylmethyl)-4-pyrimidone (1.0 g) were fused together at 170° for 50 minutes and allowed to cool. Water was added and the mixture was extracted at pH 13 with chloroform (discarded), adjusted to pH 7 and extracted a second time with chloroform. The second extract was evaporated to give 2-[2-(2-methoxybenzylthio)-ethylamino]-5-(3-pyridylmethyl)-4-pyrimidone as an oil which was treated with hydrogen chloride in ethanol and recrystallised from ethanol-ether to give the dihydrochloride m.p. 180°-183°.

Workup

  1. temperatureto cool
  2. extractionthe mixture was extracted at pH 13 with chloroform (discarded)
  3. extractionextracted a second time with chloroform
  4. extractionThe second extract
  5. customwas evaporated

Sources & evidence

ORD record
ord-c5479fcdabb14c8e95b2dc0bdd90fb88
Source dataset
uspto-grants-1985_01
Patent number
US04496567

Reaction notes

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