Triethylamine → Butyl-(6-chloro-2,5-dimethylpyrimidin-4-yl)-ethylamine

HRID 1245660Notes

Reaction equation

HRID 1245660 reaction equation
[CH3:1][C:2]1[N:7]=[C:6](Cl)[C:5]([CH3:9])=[C:4]([Cl:10])[N:3]=1.C(N(CC)CC)C.[CH2:18]([NH:22][CH2:23][CH3:24])[CH2:19][CH2:20][CH3:21]>C(#N)C.O.Cl>[CH2:18]([N:22]([C:6]1[C:5]([CH3:9])=[C:4]([Cl:10])[N:3]=[C:2]([CH3:1])[N:7]=1)[CH2:23][CH3:24])[CH2:19][CH2:20][CH3:21]

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 25914ButylethylamineHCID 2370134,6-Dichloro-2,5-dimethylpyrimidine

Product 1

HCID 21912306Butyl-(6-chloro-2,5-dimethylpyrimidin-4-yl)-ethylamineYield 64.3%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

A mixture of 2,5-dimethyl-4,6-dichloro-pyrimidine (0.999 g, 5.64 mmol) in 5 ml of acetonitrile was treated with triethylamine (0.571 g, 5.65 mmol) and N-butyl-ethyl-amine (0.570 g, 5.65 mmol) and heated at reflux overnight. The mixture was cooled, diluted 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 0.877 g (64%) of title compound as a yellow oil. 1H NMR (CDCl3) δ 0.90 (t, 3H), 1.15 (t, 3H), 1.22–1.36(m, 2H), 1.5–1.6(m, 2H), 2.20 (s, 3H), 2.45 (s, 3H), 3.25–3.48 (m, 4H) ppm.

Workup

  1. temperatureheated
  2. temperatureat reflux overnight
  3. temperatureThe mixture was cooled
  4. extractionextracted with ethyl acetate
  5. washwashed with brine
  6. customdried
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-dcafa09a684f40d6994340e951cdf915
Source dataset
uspto-grants-2006_10
Patent number
US07125880B1

Reaction notes

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