Aniline → 4,6-Dichloro-N-phenyl-2-pyrimidinamine

HRID 1352883Notes

Reaction equation

HRID 1352883 reaction equation
Cl[C:2]1[N:7]=[C:6]([Cl:8])[CH:5]=[C:4]([Cl:9])[N:3]=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>O1CCCC1>[Cl:9][C:4]1[CH:5]=[C:6]([Cl:8])[N:7]=[C:2]([NH:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[N:3]=1

Participants

5

Reactant 3

HCID 6115AnilineHCID 773782,4,6-TrichloropyrimidineHCID 81531Diisopropylethylamine

Product 1

HCID 6171324,6-Dichloro-N-phenyl-2-pyrimidinamine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 2,4,6-trichloropyrimidine (5.5 g, 30 mmol) in tetrahydrofuran (15 mL) was added dropwise to a solution of aniline (2.8 mL, 1 equivalent) in tetrahydrofuran (25 mL). N,N-diisopropylethylamine (5.2 mL) was added and the solution was stirred at room temperature overnight. The solvent was removed and the crude material was purified by flash chromatography on silica gel. The column was eluted with 3% ethyl acetate in hexane, followed by 15% ethyl acetate in hexane. The eluent was removed, giving 4,6-dichloro-N-phenyl-2-pyrimidinamine (1.11 g, 4.6 mmol, 15%, Rf=0.4 in 3% ethyl acetate in hexane).

Workup

  1. customThe solvent was removed
  2. customthe crude material was purified by flash chromatography on silica gel
  3. washThe column was eluted with 3% ethyl acetate in hexane
  4. customThe eluent was removed

Sources & evidence

ORD record
ord-5438e423b0084e1cad4194e0a9107a0d
Source dataset
uspto-grants-2007_05
Patent number
US07220775B2

Reaction notes

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