3,5-Dimethoxyaniline → {5-[(3,5-Dimethoxy-phenylimino)-methyl]-2-methylsulfanyl-pyrimidin-4-yl}-ethyl-amine

HRID 1783531Notes

Reaction equation

HRID 1783531 reaction equation
[CH2:1]([NH:3][C:4]1[C:9]([CH:10]=O)=[CH:8][N:7]=[C:6]([S:12][CH3:13])[N:5]=1)[CH3:2].[CH3:14][O:15][C:16]1[CH:17]=[C:18]([CH:20]=[C:21]([O:23][CH3:24])[CH:22]=1)[NH2:19]>C(O)(=O)C>[CH3:24][O:23][C:21]1[CH:20]=[C:18]([N:19]=[CH:10][C:9]2[C:4]([NH:3][CH2:1][CH3:2])=[N:5][C:6]([S:12][CH3:13])=[N:7][CH:8]=2)[CH:17]=[C:16]([O:15][CH3:14])[CH:22]=1

Participants

4

Reactant 2

HCID 663013,5-DimethoxyanilineHCID 107504444-(Ethylamino)-2-(methylthio)pyrimidine-5-carbaldehyde

Product 1

HCID 68858962{5-[(3,5-Dimethoxy-phenylimino)-methyl]-2-methylsulfanyl-pyrimidin-4-yl}-ethyl-amineYield 92%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a stirred suspension of 4-ethylamino-2-methylsulfanyl-pyrimidine-5-carbaldehyde (5.0 g, 25.09 mmol, made by the method described in J. Med. Chem., 1998; 41(17):3276-3292) and 3,5-dimethoxyaniline (3.84 g, 25.09 mmol) water (190 mL) was added glacial acetic acid (5 mL). The reaction mixture was stirred at ambient temperature for 24 hours and the suspension filtered. The insoluble product was dried on the filter to afford 7.79 g (92%) of the titled compound: mp 100-105° C.

Workup

  1. filtrationthe suspension filtered
  2. customThe insoluble product was dried on the
  3. filtrationfilter

Sources & evidence

ORD record
ord-8e910fbde0ea4406a22d1d0e036578c9
Source dataset
uspto-grants-2009_03
Patent number
US07501425B1

Reaction notes

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