5-(4-Methoxybenzyl)-2-methylthio-4-pyrimidone → 2-[3-(N-propyl-N-pyrid-2-ylamino)propylamino]-5-(4-methoxybenzyl)pyrimid-4-one

HRID 464369Notes

Reaction equation

HRID 464369 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][N:5]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=1)[CH2:6][CH2:7][CH3:8].CS[C:17]1[NH:22][C:21](=[O:23])[C:20]([CH2:24][C:25]2[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=2)=[CH:19][N:18]=1>>[CH2:6]([N:5]([CH2:4][CH2:3][CH2:2][NH:1][C:17]1[NH:22][C:21](=[O:23])[C:20]([CH2:24][C:25]2[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=2)=[CH:19][N:18]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=1)[CH2:7][CH3:8]

Participants

3

Reactant 2

HCID 129515135-(4-Methoxybenzyl)-2-methylthio-4-pyrimidoneHCID 201866052-[N-(3-aminopropyl)-N-propylamino]pyridine

Product 1

HCID 202628902-[3-(N-propyl-N-pyrid-2-ylamino)propylamino]-5-(4-methoxybenzyl)pyrimid-4-one

Procedure

2-[N-(3-aminopropyl)-N-propylamino]pyridine (1.0 g) and 2-methylthio-5-(4-methoxybenzyl)pyrimid-4-one (0.88 g) were fused together on an oil bath at 160° C. for 2.5 hr. On cooling the residue was crystallized from ethanol/water to give a white solid which on recrystallization from acetone/water gave 2-[3-(N-propyl-N-pyrid-2-ylamino)propylamino]-5-(4-methoxybenzyl)pyrimid-4-one 1 H2O; 1.27 g (79%) m.p. indeterminate.

Workup

  1. temperatureOn cooling the residue
  2. customwas crystallized from ethanol/water
  3. customto give a white solid which
  4. customon recrystallization from acetone/water

Sources & evidence

ORD record
ord-cec57dabe5d14b18bebd0ee16c6d05d8
Source dataset
uspto-grants-1985_10
Patent number
US04547506

Reaction notes

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