3,4,5-Trimethoxyaniline → HCID 21995262, compound

HRID 1977687Notes

Reaction equation

HRID 1977687 reaction equation
Cl[C:2]1[N:7]=[C:6](Cl)[CH:5]=[CH:4][N:3]=1.[CH3:9][O:10][C:11]1[CH:12]=[C:13]([CH:15]=[C:16]([O:20][CH3:21])[C:17]=1[O:18][CH3:19])[NH2:14]>>[CH3:21][O:20][C:16]1[CH:15]=[C:13]([NH:14][C:2]2[N:7]=[C:6]([NH:14][C:13]3[CH:15]=[C:16]([O:20][CH3:21])[C:17]([O:18][CH3:19])=[C:11]([O:10][CH3:9])[CH:12]=3)[CH:5]=[CH:4][N:3]=2)[CH:12]=[C:11]([O:10][CH3:9])[C:17]=1[O:18][CH3:19]

Participants

3

Reactant 2

HCID 322853,4,5-TrimethoxyanilineHCID 775312,4-Dichloropyrimidine

Product 1

HCID 21995262HCID 21995262, compoundYield 15.2%

Procedure

A solution of 2,4-dichloropyrimidine (1.0 g, 6.7 mmol), 3,4,5-trimethoxyaniline (2.5 g, 13.4 mmol) and triethylamnine (1.8 ml, 12.6 mmol) was heated at reflux for 5 h. On cooling the resulting precipitate was collected and recrystallised from ethyl acetate to give the title compound (450 mg) as a purple solid m.p. 180°. MS m/z 443 (M+H)+.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 5 h
  3. temperatureOn cooling the resulting precipitate
  4. customwas collected
  5. customrecrystallised from ethyl acetate

Sources & evidence

ORD record
ord-e24bb0d21bea45a3a127466ea273d3e0
Source dataset
uspto-grants-2001_05
Patent number
US06235746B1

Reaction notes

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