4-Chloroaniline → 2-chloro-N-(4-chlorophenyl)-6-phenylpyrimidin-4-amine

HRID 1942964Notes

Reaction equation

HRID 1942964 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[CH:5]=[C:4]([C:9]2[C:14](F)=[CH:13][CH:12]=[CH:11][C:10]=2Cl)[N:3]=1.[Cl:17][C:18]1[CH:24]=[CH:23][C:21]([NH2:22])=[CH:20][CH:19]=1.C([N-]C(C)C)(C)C.[Li+].C(OCC)(=O)C.CCCCCC>C1COCC1>[Cl:1][C:2]1[N:7]=[C:6]([NH:22][C:21]2[CH:23]=[CH:24][C:18]([Cl:17])=[CH:19][CH:20]=2)[CH:5]=[C:4]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[N:3]=1

Participants

6

Reactant 4

HCID 78124-ChloroanilineHCID 2724682Lithium diisopropylamideHCID 21226206Ethyl acetate hexaneHCID 866614712,4-Dichloro-6-(2-chloro-6-fluorophenyl)pyrimidine

Product 1

HCID 866614732-chloro-N-(4-chlorophenyl)-6-phenylpyrimidin-4-amine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 1 mmol of 2,4-dichloro-6-phenylpyrimidine (X) and 4-chloroaniline in 4 mL of dry THF was added 1 mmol (0.5 mL, 2M in THF/heptane/ethylbenzene) of lithium diisopropylamide. The reaction was followed by TLC (30% ethyl acetate/hexane). The reaction mixture was partitioned between ethyl acetate and saturated aqueous sodium bicarbonate and the organic layers were dried over magnesium sulfate and concentrated under reduced pressure. The mixture was purified by chromatography on silica gel with elution by 30% ethyl acetate/hexanes to afford 70 mg of 2-chloro-N-(4-chlorophenyl)-6-phenylpyrimidin-4-amine (XII) as an amorphous solid. ESI/MS 315.883, 317.915 (M+H).

Workup

  1. customThe reaction mixture was partitioned between ethyl acetate and saturated aqueous sodium bicarbonate
  2. dry with materialthe organic layers were dried over magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe mixture was purified by chromatography on silica gel with elution by 30% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-5ed2b0220b5f448aa94ab4c4bc6b9d07
Source dataset
uspto-grants-2013_03
Patent number
US08389718B2

Reaction notes

Loading…