Water → HCID 15871395, compound

HRID 1740850Notes

Reaction equation

HRID 1740850 reaction equation
Cl[C:2]1[C:7]([CH3:8])=[C:6]([CH3:9])[N:5]=[C:4]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[N:3]=1.[NH2:16][CH2:17][C:18]([N:20]([CH2:24][CH2:25][CH3:26])[CH2:21][CH2:22][CH3:23])=[O:19].C(N(CC)CC)C.O>C(Cl)(Cl)Cl>[CH3:8][C:7]1[C:2]([NH:16][CH2:17][C:18]([N:20]([CH2:24][CH2:25][CH3:26])[CH2:21][CH2:22][CH3:23])=[O:19])=[N:3][C:4]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[N:5][C:6]=1[CH3:9]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 127424812-amino-N,N-dipropyl-acetamideHCID 134879354-Chloro-5,6-dimethyl-2-phenylpyrimidine

Product 1

HCID 15871395HCID 15871395, compoundYield 83.5%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 4-chloro-5,6-dimethyl-2-phenylpyrimidine (1.0 g), 2-amino-N,N-dipropylacetamide (0.87 g) and triethylamine (0.55 g) is refluxed with stirring at 150° C. for three hours. To the reaction mixture are added water and chloroform, and the chloroform layer is collected, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue is purified by silica gel column chromatography (eluent; chloroform), and recrystallized from a mixture of diethyl ether and n-hexane to give the desired compound (1.3 g), m.p. 79-80° C.

Workup

  1. temperatureis refluxed
  2. customthe chloroform layer is collected
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue is purified by silica gel column chromatography (eluent; chloroform)
  6. customrecrystallized from a mixture of diethyl ether and n-hexane

Sources & evidence

ORD record
ord-1eb63f1fe4da4e9c929a4090258980c3
Source dataset
uspto-grants-1999_10
Patent number
US05972946

Reaction notes

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