Aniline → 2-Chloro-N-phenylpyrimidin-4-amine

HRID 347755Notes

Reaction equation

HRID 347755 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[CH:5]=[CH:4][N:3]=1.[NH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(N(CC)CC)C>CCO>[Cl:1][C:2]1[N:7]=[C:6]([NH:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 6115AnilineHCID 8471TriethylamineHCID 775312,4-Dichloropyrimidine

Product 1

HCID 219953492-Chloro-N-phenylpyrimidin-4-amine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2,4-Dichloropyrimidine (3.75 g, 25 mmol) was dissolved in EtOH (12 ml) and treated with aniline (2.27 ml, 25 mmol) and triethylamine (3.82 ml, 27.2 mmol). The reaction mixture was heated to reflux for 6 hours, partitioned between EtOAc and water. The organic phase was washed with 1M HCl, dried over MgSO4 and evaporated to obtain a cream coloured solid. This material was purified by chromatography (25–50% EtOAc in isohexane) to give the title product as an off white solid. NMR (300 MHz) 6.73 (d, 1H), 7.08 (t, 1H), 7.35 (t, 2H), 7.57 (d, 2H), 8.12 (d, 1H), 9.95 (brs, 1H); m/z: (ES+) 206 (MH+).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 6 hours
  3. custompartitioned between EtOAc and water
  4. washThe organic phase was washed with 1M HCl
  5. dry with materialdried over MgSO4
  6. customevaporated
  7. customto obtain a cream
  8. customThis material was purified by chromatography (25–50% EtOAc in isohexane)

Sources & evidence

ORD record
ord-d1053c30bb8f4c7a9cc9259f1d3309c4
Source dataset
uspto-grants-2007_02
Patent number
US07176212B2

Reaction notes

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