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

HRID 967944Notes

Reaction equation

HRID 967944 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-8bfd5ebe169e48d8b0385cf053d38291
Source dataset
uspto-grants-2005_10
Patent number
US06956047B1

Reaction notes

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