2-Nitroamino-5-(2-methoxy-4-pyridyl)methyl-4-pyrimidone → 2-(4-Dimethylaminomethyl-2-pyridylmethylthio)ethylamino-5-(2-methoxy-4-pyridylmethyl)-4-pyrimidone

HRID 365005Notes

Reaction equation

HRID 365005 reaction equation
[CH3:1][N:2]([CH2:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]([CH2:11][S:12][CH2:13][CH2:14][NH2:15])[CH:6]=1)[CH3:3].[N+](N[C:20]1[NH:25][C:24](=[O:26])[C:23]([CH2:27][C:28]2[CH:33]=[CH:32][N:31]=[C:30]([O:34][CH3:35])[CH:29]=2)=[CH:22][N:21]=1)([O-])=O>N1C=CC=CC=1>[CH3:3][N:2]([CH2:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]([CH2:11][S:12][CH2:13][CH2:14][NH:15][C:20]2[NH:25][C:24](=[O:26])[C:23]([CH2:27][C:28]3[CH:33]=[CH:32][N:31]=[C:30]([O:34][CH3:35])[CH:29]=3)=[CH:22][N:21]=2)[CH:6]=1)[CH3:1]

Participants

4

Reactant 2

HCID 127838332-Nitroamino-5-(2-methoxy-4-pyridyl)methyl-4-pyrimidoneHCID 132773272-(4-Dimethylaminomethyl-2-pyridylmethylthio)ethylamine

Product 1

HCID 132926052-(4-Dimethylaminomethyl-2-pyridylmethylthio)ethylamino-5-(2-methoxy-4-pyridylmethyl)-4-pyrimidoneYield 61.9%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 2-(4-dimethylaminomethyl-2-pyridylmethylthio)ethylamine (1 g) and 2-nitroamino-5-(2-methoxy-4-pyridylmethyl)-4-pyrimidone (1.23 g) was refluxed in pyridine (6 ml) for 10 hours, concentrated in vacuo and chromatographed on silica gel column eluted with ethyl acetate-ethanol-28% W:W aqueous ammonia (by volume 10:15:2). Recrystallisation from acetonitrile:ether (1:5) gave 2-[2-(4-dimethylaminomethyl-2-pyridylmethylthio)ethylamino-5-(2-methoxy-4-pyridylmethyl)-4-pyrimidone (1.21 g) m.p. 65°-74° C.

Workup

  1. concentrationconcentrated in vacuo
  2. customchromatographed on silica gel column
  3. washeluted with ethyl acetate-ethanol-28% W
  4. customRecrystallisation from acetonitrile:ether (1:5)

Sources & evidence

ORD record
ord-7008b9be1ac2482791a4f9fe7175b59f
Source dataset
uspto-grants-1986_08
Patent number
US04607107

Reaction notes

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