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

HRID 967941

Reaction equation

HRID 967941 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 65%

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 (65%) 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-3f0ac3938b694f32a6923d3678ec1409
Source dataset
uspto-grants-2005_10
Patent number
US06956047B1

Linked notes

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