2,4,6-Trimethylaniline → N-Butyl-N-ethyl-2-methyl-5-ethyl-N'-(2,4,6-trimethylphenyl)-pyrimidine-4,6-diamine
Reaction equation
[CH2:1]([N:5]([C:8]1[C:13]([CH2:14][CH3:15])=[C:12](Cl)[N:11]=[C:10]([CH3:17])[N:9]=1)[CH2:6][CH3:7])[CH2:2][CH2:3][CH3:4].[CH3:18][C:19]1[CH:25]=[C:24]([CH3:26])[CH:23]=[C:22]([CH3:27])[C:20]=1[NH2:21]>>[CH2:1]([N:5]([CH2:6][CH3:7])[C:8]1[C:13]([CH2:14][CH3:15])=[C:12]([NH:21][C:20]2[C:22]([CH3:27])=[CH:23][C:24]([CH3:26])=[CH:25][C:19]=2[CH3:18])[N:11]=[C:10]([CH3:17])[N:9]=1)[CH2:2][CH2:3][CH3:4]Participants
3
Procedure
A mixture of butyl-(6-chloro-2-methyl-5-ethyl-pyrimidin-4-yl)-ethylamine (200 mg, 0.78 mmol) and 2,4,6-trimethylaniline (0.963 g, 7.1 mmol) was heated at reflux for 4 hours. The mixture was quenched with water and extracted with ethyl acetate. The organic layer was washed with saturated potassium carbonate and brine, dried and concentrated to give a dark oil. The oil was distilled to give 579 mg of the dark oil which was then purified through silica gel column chromatography using chloroform as eluent to give the title compound as a brown oil. 1H NMR (CDCl3) δ 0.93 (t, 3H), 1.14 (t, 3H), 1.1-1.4 (m, 4H), 1.45-1.60 (m, 2H), 2.17 (s, 6H), 2.30 (s, 3H), 2.33 (s, 3H), 3.2-3.4 (m, 4H), 6.90 (s, 2H) ppm.
Workup
- temperaturewas heated
- temperatureat reflux for 4 hours
- customThe mixture was quenched with water
- extractionextracted with ethyl acetate
- washThe organic layer was washed with saturated potassium carbonate and brine
- customdried
- concentrationconcentrated
- customto give a dark oil
- distillationThe oil was distilled
Sources & evidence
- ORD record
- ord-1b8795cfa78543deab4e365cbd19f96f
- Source dataset
- uspto-grants-2005_10
- Patent number
- US06956047B1
Reaction notes
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