HCID 22378694, compound → HCID 22378989, compound

HRID 895492Notes

Reaction equation

HRID 895492 reaction equation
Cl[C:2]1[N:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:5]=[C:4]([NH:14][CH2:15][CH2:16][NH:17][C:18](=[O:20])[CH3:19])[CH:3]=1>C(N)CN>[NH2:14][CH2:15][CH2:16][NH:17][C:2]1[N:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:5]=[C:4]([NH:14][CH2:15][CH2:16][NH:17][C:18](=[O:20])[CH3:19])[CH:3]=1

Participants

3

Reactant 1

HCID 22378694HCID 22378694, compound

Product 1

HCID 22378989HCID 22378989, compoundYield 164.6%

Reagents, catalysts & solvents 1

HCID 3301EthylenediamineSolvent

Procedure

N-{2-[(6-Chloro-2-phenylpyrimidin-4-yl)amino]ethyl}acetamide (100 mg) was dissolved in ethylenediamine (5 ml) and the stirred under reflux for 4 hrs. The reaction mixture was then cooled to ambient temperature and the solvent removed in vacuo. Purification via flash chromatography on silica gel eluting first with a mixture of ethyl acetate and methanol (9:1 v/v) then a mixture of ethyl acetate, methanol and ammonium hydroxide (80:20:2 v/v/v) to furnish the title compound (89 mg).

Workup

  1. temperatureunder reflux for 4 hrs
  2. customthe solvent removed in vacuo
  3. customPurification via flash chromatography on silica gel eluting
  4. additionfirst with a mixture of ethyl acetate and methanol (9:1 v/v)
  5. additiona mixture of ethyl acetate, methanol and ammonium hydroxide (80:20:2 v/v/v)

Sources & evidence

ORD record
ord-92d59e34fc28426d8432fee869e6a7b7
Source dataset
uspto-grants-2005_07
Patent number
US06916804B2

Reaction notes

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