2-(Benzylsulfanyl)ethan-1-amine → 5-(3-Pyridylmethyl)-4-pyrimidone

HRID 2413158Notes

Reaction equation

HRID 2413158 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][C:8]2[C:9](=[O:16])[NH:10][C:11](SC)=[N:12][CH:13]=2)[CH:2]=1.C(SCCN)C1C=CC=CC=1>N1C=CC=CC=1>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][C:8]2[C:9](=[O:16])[NH:10][CH:11]=[N:12][CH:13]=2)[CH:2]=1

Participants

4

Reactant 2

HCID 311982-(Benzylsulfanyl)ethan-1-amineHCID 12783823HCID 12783823, compound

Product 1

HCID 204481775-(3-Pyridylmethyl)-4-pyrimidone

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 5-(3-pyridylmethyl)-2-methylthio-4-pyrimidone (1.0 g),2-(benzylthio)ethylamine (1.06 g) and dry pyridine (30 ml) was heated under reflux for 40 hours and evaporated to dryness. Water was added to the residue and the mixture was extracted with chloroform (discarded). The aqueous phase was adjusted to pH 7 and was extracted with chloroform. This extract was evaporated to dryness and the residue was recrystallised from ethanol to give 2-[2-benzylthio)ethylamino]-5-(3-pyridylmethyl)-4-pyrimidone m.p. 145°-148°.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 40 hours
  3. customevaporated to dryness
  4. additionWater was added to the residue
  5. extractionthe mixture was extracted with chloroform (discarded)
  6. extractionwas extracted with chloroform
  7. customThis extract was evaporated to dryness
  8. customthe residue was recrystallised from ethanol

Sources & evidence

ORD record
ord-55ab22f80d5047df8439e58bf2413269
Source dataset
uspto-grants-1985_01
Patent number
US04496567

Reaction notes

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