5-(4-Chlorobenzyl)-2-methylthiopyrimid-4-one → 2-[3-(N-benzyl-N-pyrid-2-ylamino) propylamino]-5-(4-chlorobenzyl)pyrimid-4-one

HRID 464347Notes

Reaction equation

HRID 464347 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][N:5]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=1)[CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.CS[C:21]1[NH:26][C:25](=[O:27])[C:24]([CH2:28][C:29]2[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][CH:30]=2)=[CH:23][N:22]=1>>[CH2:6]([N:5]([CH2:4][CH2:3][CH2:2][NH:1][C:21]1[NH:26][C:25](=[O:27])[C:24]([CH2:28][C:29]2[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][CH:30]=2)=[CH:23][N:22]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

3

Reactant 2

HCID 129459805-(4-Chlorobenzyl)-2-methylthiopyrimid-4-oneHCID 201503642-[N-(3-aminopropyl)-N-benzylamino)pyridine

Product 1

HCID 541841732-[3-(N-benzyl-N-pyrid-2-ylamino) propylamino]-5-(4-chlorobenzyl)pyrimid-4-one

Procedure

2-[N-(3-aminopropyl)-N-benzylamino]pyridine (1.45 g) and 2-methylthio-5-(4-chlorobenzyl)pyrimid-4-one (1.33 g) were fused together on an oil bath at 160° C. for 3 hr. On cooling, the residue was crystallised from ethanol and then chromatographed (silica gel, chloroform). Fractions containing the required product were stripped and the residue recrystallised from ethanol to give 2-[3-(N-benzyl-N-pyrid-2-ylamino) propylamino]-5-(4-chlorobenzyl)pyrimid-4-one 0.25H2O, 0.9 g (39%) mp 80°-86° C.

Workup

  1. temperatureOn cooling
  2. customthe residue was crystallised from ethanol
  3. customchromatographed (silica gel, chloroform)
  4. additionFractions containing the required product
  5. customthe residue recrystallised from ethanol

Sources & evidence

ORD record
ord-a6211da6756f4242949dc93578ad445b
Source dataset
uspto-grants-1985_10
Patent number
US04547506

Reaction notes

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