2,4,6-Trimethylaniline → HCID 21912272, compound

HRID 1831618Notes

Reaction equation

HRID 1831618 reaction equation
[CH2:1]([N:5]([C:8]1[CH:13]=[C:12](Cl)[N:11]=[C:10]([CH3:15])[N:9]=1)[CH2:6][CH3:7])[CH2:2][CH2:3][CH3:4].[CH3:16][C:17]1[CH:23]=[C:22]([CH3:24])[CH:21]=[C:20]([CH3:25])[C:18]=1[NH2:19]>>[CH2:1]([N:5]([CH2:6][CH3:7])[C:8]1[CH:13]=[C:12]([NH:19][C:18]2[C:20]([CH3:25])=[CH:21][C:22]([CH3:24])=[CH:23][C:17]=2[CH3:16])[N:11]=[C:10]([CH3:15])[N:9]=1)[CH2:2][CH2:3][CH3:4]

Participants

3

Reactant 2

HCID 69132,4,6-TrimethylanilineHCID 21912249HCID 21912249, compound

Product 1

HCID 21912272HCID 21912272, compound

Procedure

A mixture of butyl-(6-chloro-2-methyl-pyrimidin-4-yl)-ethylamine (1.006 g, 4.42 mmol), and 2,4,6-trimethylaniline (3 ml) was heated at reflux overnight. The mixture was quenched with water and extracted with ethyl acetate. The organic layer was dried and concentrated to give 2.862 g of a brown oil. The oil was purified through silica gel column chromatography to give 981 mg (68%) of title compound as a yellow oil. 1H NMR (CDCl3) δ 0.80 (t, 3H), 1.1–1.3 (m, 2H), 1.3–1.5 (m, 2H), 2.17 (s, 6H), 2.27 (s, 3H), 2.41 (s, 3H), 3.2 (m, 2H), 3.36 (m, 2H), 4.66 (s, 1H), 6.90 (s, 2H) ppm.

Workup

  1. temperaturewas heated
  2. temperatureat reflux overnight
  3. customThe mixture was quenched with water
  4. extractionextracted with ethyl acetate
  5. customThe organic layer was dried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-baefc19e912848919bd3a1fdc8518bb9
Source dataset
uspto-grants-2006_06
Patent number
US07067664B1

Reaction notes

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