2,4,6-Trimethylaniline → N-Butyl-N-ethyl-2,5-dimethyl-N'-(2,4,6-trimethylphenyl)-pyrimidine-4,6-diamine

HRID 1245661Notes

Reaction equation

HRID 1245661 reaction equation
[CH2:1]([N:5]([C:8]1[C:13]([CH3:14])=[C:12](Cl)[N:11]=[C:10]([CH3:16])[N:9]=1)[CH2:6][CH3:7])[CH2:2][CH2:3][CH3:4].[CH3:17][C:18]1[CH:24]=[C:23]([CH3:25])[CH:22]=[C:21]([CH3:26])[C:19]=1[NH2:20].C(N(C(C)C)CC)(C)C>>[CH2:1]([N:5]([CH2:6][CH3:7])[C:8]1[C:13]([CH3:14])=[C:12]([NH:20][C:19]2[C:21]([CH3:26])=[CH:22][C:23]([CH3:25])=[CH:24][C:18]=2[CH3:17])[N:11]=[C:10]([CH3:16])[N:9]=1)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 3

HCID 69132,4,6-TrimethylanilineHCID 81531DiisopropylethylamineHCID 21912306Butyl-(6-chloro-2,5-dimethylpyrimidin-4-yl)-ethylamine

Product 1

HCID 9840906N-Butyl-N-ethyl-2,5-dimethyl-N'-(2,4,6-trimethylphenyl)-pyrimidine-4,6-diamineYield 103.1%

Conditions

Temperature
220 °C

Procedure

A mixture of butyl-(6-chloro-2,5-dimethyl-pyrimidin-4-yl)-ethylamine (398 mg, 1.65 mmol), 2,4,6-trimethylaniline (4.04 g, 30 mmol) and diisopropyl-ethyl-amine (200 mg, 1.55 mmol) was heated at 210 to 230° C. overnight. The mixture was quenched with water and dilute hydrogen chloride, and extracted with ethyl acetate. The organic layer was neutralized with saturated potassium carbonate, washed with brine, dried and concentrated to give a dark oil. The oil was distilled to give 579 mg of dark oil which was then purified through silica gel column chromatography using 1:1 hexane to chloroform as eluent to give 327 mg of title compound as a yellow solid. 1H NMR (CDCl3) δ 0.92 (t, 3H), 1.14 (t, 3H), 1.2–1.4 (m, 2h), 1.45–1.60 (m, 2H), 1.85 (s, 3H), 2.16 (s, 6H), 2.30 (s, 3H), 2.33 (s, 3H), 3.2–3.4 (m, 4H), 5.8 (brs, 1H), 6.90 (s, 2H) ppm.

Workup

  1. customThe mixture was quenched with water and dilute hydrogen chloride
  2. extractionextracted with ethyl acetate
  3. washwashed with brine
  4. customdried
  5. concentrationconcentrated
  6. customto give a dark oil
  7. distillationThe oil was distilled

Sources & evidence

ORD record
ord-72131e0b0dd542e8aa06f6d400a0251a
Source dataset
uspto-grants-2006_10
Patent number
US07125880B1

Reaction notes

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