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

HRID 1760657Notes

Reaction equation

HRID 1760657 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]([NH:23][CH2:24][CH2:25][C:6]1[C:5]([CH2:9][CH3:10])=[C:4]([Cl:11])[N:3]=[C:2]([CH3:1])[N:7]=1)[CH2:20][CH2:21][CH3:22]

Participants

7

Reactant 3

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

Product 1

HCID 53883936Butyl-(6-chloro-2-methyl-5-ethyl-pyrimidin-4-yl)ethyl-amineYield 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-a957592e8bb2410e801a2c976a02a1e8
Source dataset
uspto-grants-2005_01
Patent number
US06844351B1

Reaction notes

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