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

HRID 1760656Notes

Reaction equation

HRID 1760656 reaction equation
[CH3:1][C:2]1[N:7]=[C:6](Cl)[CH:5]=[C:4]([Cl:9])[N:3]=1.[CH2:10]([NH:14][CH2:15][CH3:16])[CH2:11][CH2:12][CH3:13]>C(#N)C.O>[CH2:10]([NH:14][CH2:15][CH2:16][C:6]1[CH:5]=[C:4]([Cl:9])[N:3]=[C:2]([CH3:1])[N:7]=1)[CH2:11][CH2:12][CH3:13]

Participants

5

Reactant 2

HCID 25914ButylethylamineHCID 2349974,6-Dichloro-2-methylpyrimidine

Product 1

HCID 53834625Butyl-(6-chloro-2-methyl-pyrimidin-4-yl)ethyl-amineYield 100%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

A mixture of 2-methyl-4,6-dichloro-pyrimidine (1.63 g, 10 mmol) in 5 ml of acetonitrile was treated with N-butyl-ethyl-amine (2.000 g, 20 mmol) and heated at reflux for 0.5 hours. The mixture was cooled, diluted with water and extracted with ethyl acetate. The organic layer was washed with brine, dried and concentrated to give 2.271 g (100%) of title compound as a light-brown oil. 1H NMR (CDCl3) δ 0.93 (t, 3H), 1.13 (t, 3H), 1.22-1.36 (m, 2H), 1.45-1.6 (m, 2H), 2.43 (s, 3H), 3.25-3.60 (m, 4H), 6.15 (s, 1H) ppm.

Workup

  1. temperatureheated
  2. temperatureat reflux for 0.5 hours
  3. temperatureThe mixture was cooled
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with brine
  6. customdried
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-7ac1c45adadc48a2be6067cf0fdc4cde
Source dataset
uspto-grants-2005_01
Patent number
US06844351B1

Reaction notes

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