Methylamine → 1,6-Dimethyl-2-(1-methoxypropyl)-3-benzyloxy-pyridin-4(1H)-one

HRID 1279408Notes

Reaction equation

HRID 1279408 reaction equation
[CH2:1]([N:3]1C=CC(=O)C(OCC2C=CC=CC=2)=C1COC)C.[CH3:21][O:22][CH:23]([C:26]1O[C:28]([CH3:41])=[CH:29][C:30](=[O:40])[C:31]=1[O:32][CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[CH2:24][CH3:25].CN>>[CH3:1][N:3]1[C:28]([CH3:41])=[CH:29][C:30](=[O:40])[C:31]([O:32][CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)=[C:26]1[CH:23]([O:22][CH3:21])[CH2:24][CH3:25]

Participants

4

Reactant 3

HCID 6329MethylamineHCID 186788002-(1-methoxypropyl)-3-benzyloxy-6-methyl-pyran-4(1H)-oneHCID 186788071-Ethyl-2-methoxymethyl-3-benzyloxy-pyridin-4(1H)-one

Product 1

HCID 186787911,6-Dimethyl-2-(1-methoxypropyl)-3-benzyloxy-pyridin-4(1H)-oneYield 37.6%

Procedure

In an analogous procedure in the preparation of 1-ethyl-2-methoxymethyl-3-benzyloxy-pyridin-4(1H)-one using 2-(1-methoxypropyl)-3-benzyloxy-6-methyl-pyran-4(1H)-one 4.32 g (15 mmol, 1 eq.) and 3.49 g (45 mmol, 3 eq.) of 40% aqueous methlamine yielded the title compound (1.7 g, 37.6%) after purification by column chromatography on silica gel (eluant: 15% CH3OH/85% CHCl3) as a yellow oil.

Sources & evidence

ORD record
ord-9ef0e7007f014d5a800856dcb0f34da8
Source dataset
uspto-grants-2002_09
Patent number
US06448273B1

Reaction notes

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