2-[N-(4-aminobutyl)-N-propylamino]pyridine → 2-[4-(N-propyl-N-pyrid-2-ylamino)butylamino]5-(4-fluorobenzyl)pyrimid-4-one

HRID 464362Notes

Reaction equation

HRID 464362 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][N:6]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=1)[CH2:7][CH2:8][CH3:9].CS[C:18]1[NH:23][C:22](=[O:24])[C:21]([CH2:25][C:26]2[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=2)=[CH:20][N:19]=1>>[CH2:7]([N:6]([CH2:5][CH2:4][CH2:3][CH2:2][NH:1][C:18]1[NH:23][C:22](=[O:24])[C:21]([CH2:25][C:26]2[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=2)=[CH:20][N:19]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=1)[CH2:8][CH3:9]

Participants

3

Reactant 2

HCID 201866172-[N-(4-aminobutyl)-N-propylamino]pyridineHCID 202628785-(4-Fluorobenzyl)-2-methylthio-4-pyrimidone

Product 1

HCID 536682962-[4-(N-propyl-N-pyrid-2-ylamino)butylamino]5-(4-fluorobenzyl)pyrimid-4-one

Procedure

2-[N-(4-aminobutyl)-N-propylamino]pyridine (1.24 g) and 2-methylthio-5-(4-fluorobenzyl)pyrimid-4-one (1.25 g) were fused together on an oil bath at 160° C. for 2.5 hr. On cooling the residue was crystallised twice from ethanol/water to give 2-[4-(N-propyl-N-pyrid-2-ylamino)butylamino]5-(4-fluorobenzyl)pyrimid-4-one 1.25H2O, 0.56 g (26.%) mp indeterminate.

Workup

  1. temperatureOn cooling the residue
  2. customwas crystallised twice from ethanol/water

Sources & evidence

ORD record
ord-cadd9e8859ab4e4e8a5d4d2efe65cbdc
Source dataset
uspto-grants-1985_10
Patent number
US04547506

Reaction notes

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