Aniline → 5-bromo-2-chloro-N-phenylpyrimidin-4-amine

HRID 1759754Notes

Reaction equation

HRID 1759754 reaction equation
[Br:1][C:2]1[C:3](Cl)=[N:4][C:5]([Cl:8])=[N:6][CH:7]=1.[NH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(N(CC)C(C)C)(C)C>C(O)CCC>[NH:10]([C:3]1[C:2]([Br:1])=[CH:7][N:6]=[C:5]([Cl:8])[N:4]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 6115AnilineHCID 81531DiisopropylethylamineHCID 2899735-Bromo-2,4-dichloropyrimidine

Product 1

HCID 114033895-bromo-2-chloro-N-phenylpyrimidin-4-amine

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A solution of 5-bromo-2,4-dichloropyrimidine (6.84 g, 30.0 mmol), aniline (2.79 g, 30.0 mmol) and N,N-diisopropylethylamine (3.87 g, 30.0 mmol) in n-butanol (75 ml) was heated under reflux for 4 hours. Volatile material was removed by evaporation and the residue was dissolved in DCM (100 ml). The solution was washed with water (3×100 ml) and saturated brine (100 ml) and dried. Volatile material was removed by evaporation and the residue was purified by column chromatography, eluting with 15% ethyl acetate/isohexane, to give the product as an oil which solidified on standing (5.12 g, 60%). NMR: 7.1 (t, 1H), 7.4 (t, 2H),7.55 (d,2H), 8.4 (s,1H), 9.2 (br s, 1H); MS (MH+): 284, 286, 288.

Workup

  1. temperatureunder reflux for 4 hours
  2. customVolatile material was removed by evaporation
  3. dissolutionthe residue was dissolved in DCM (100 ml)
  4. washThe solution was washed with water (3×100 ml) and saturated brine (100 ml)
  5. customdried
  6. customVolatile material was removed by evaporation
  7. customthe residue was purified by column chromatography
  8. washeluting with 15% ethyl acetate/isohexane

Sources & evidence

ORD record
ord-9b383b0be5834761b4c6d0cb4b074fc1
Source dataset
uspto-grants-2005_01
Patent number
US06838464B2

Reaction notes

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