Triethylamine → Butyl-(6-chloro-2-methyl-5-ethyl-pyrimidin-4-yl)-ethylamine

HRID 1831619Notes

Reaction equation

HRID 1831619 reaction equation
[CH3:1][C:2]1[N:7]=[C:6](Cl)[C:5]([CH2:9][CH3:10])=[C:4]([Cl:11])[N:3]=1.C(N(CC)CC)C.[CH2:19]([NH:23][CH2:24][CH3:25])[CH2:20][CH2:21][CH3:22]>C(#N)C.O.Cl>[CH2:19]([N:23]([C:6]1[C:5]([CH2:9][CH3:10])=[C:4]([Cl:11])[N:3]=[C:2]([CH3:1])[N:7]=1)[CH2:24][CH3:25])[CH2:20][CH2:21][CH3:22]

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 25914ButylethylamineHCID 219124254,6-Dichloro-5-ethyl-2-methylpyrimidine

Product 1

HCID 21912129Butyl-(6-chloro-2-methyl-5-ethyl-pyrimidin-4-yl)-ethylamineYield 88.3%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

A mixture of 2-methyl-5-ethyl-4,6-dichloro-pyrimidine (1.009 g, 5.28 mmol) in 5 ml of acetonitrile was treated with triethylamine (0.571 g, 5.65 mmol) and N-butyl-ethyl-amine (0.540 g, 5.31 mmol) and heated at reflux overnight. The mixture was diluted with water and dilute hydrogen chloride, and extracted with ethyl acetate. The organic layer was neutralized with saturated potassium carbonate and washed with brine, dried and concentrated to give 1.193 g of yellow oil which was purified through silica gel column chromatography to give 1.157 g (86%) of title compound as a yellow oil. 1H NMR (CDCl3) δ 0.90 (t, 3H), 1.13 (t, 3H), 1.18 (t, 3H), 1.1–1.33 (m, 2H), 1.4–1.6 (m, 2h), 2.41 (s, 3H), 2.62 (q, 2H), 3.25–3.48 (m, 4H) ppm.

Workup

  1. temperatureheated
  2. temperatureat reflux overnight
  3. extractionextracted with ethyl acetate
  4. washwashed with brine
  5. customdried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-fe96d7854edd440ca34e9e51e9284035
Source dataset
uspto-grants-2006_06
Patent number
US07067664B1

Reaction notes

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