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

HRID 1627431ノート

反応式

HRID 1627431 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-e0d78f250639415aa0b04bf8a9d74a7c
出典データセット
uspto-grants-2014_07
特許番号
US08785630B2

反応ノート

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