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

HRID 1634610Notes

Reaction equation

HRID 1634610 reaction equation
[CH2:1]([N:3]1C=CC(=O)C(OCC2C=CC=CC=2)=C1COC)C.[CH2:21]([O:23][CH2:24][C:25]1O[C:27]([CH3:40])=[CH:28][C:29](=[O:39])[C:30]=1[O:31][CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[CH3:22].CN>>[CH3:1][N:3]1[C:27]([CH3:40])=[CH:28][C:29](=[O:39])[C:30]([O:31][CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)=[C:25]1[CH2:24][O:23][CH2:21][CH3:22]

Participants

4

Reactant 3

HCID 6329MethylamineHCID 186788071-Ethyl-2-methoxymethyl-3-benzyloxy-pyridin-4(1H)-oneHCID 186788202-(1-ethoxymethyl)-3-benzyloxy-6-methyl-pyran-4(1H)-one

Product 1

HCID 186788281,6-Dimethyl-2-(1-ethoxymethyl)-3-benzyloxy-pyridin-4(1H)-oneYield 61.1%

Procedure

In an analogous procedure in the preparation of 1-ethyl-2-methoxymethyl-3-benzyloxy-pyridin-4(1H)-one using 2-(1-ethoxymethyl)-3-benzyloxy-6-methyl-pyran-4(1H)-one 5.76 g (20 mmol, 1 eq.) and 4.65 g (60 mmol, 3 eq.) of 40% aqueous methylamine yielded the title compound (3.68 g, 61.1%) after purification by column chromatography on silica gel (eluant: 15% CH3OH/85% CHCl3) as a yellow oil.

Sources & evidence

ORD record
ord-e2507e1fd0e947e9a0608cd71b7c0d2b
Source dataset
uspto-grants-2003_01
Patent number
US06506911B2

Reaction notes

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