Ammonium Chloride → 2-Chloro-4-phenylpyrimidine

HRID 588553

反応式

HRID 588553 の反応式
[Cl:1][C:2]1[N:7]=[C:6](Cl)[CH:5]=[CH:4][N:3]=1.[Br-].[C:10]1([Zn+])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[Cl-].[NH4+]>C1COCC1.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[Cl:1][C:2]1[N:7]=[C:6]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:5]=[CH:4][N:3]=1

参加物

6

反応物 3

HCID 25517Ammonium ChlorideHCID 775312,4-DichloropyrimidineHCID 178419759HCID 178419759、化合物

生成物 1

HCID 6053562-Chloro-4-phenylpyrimidine

試薬・触媒・溶媒 2

HCID 11979704Tetrakis(triphenylphosphine)palladium触媒HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
50 °C

実験手順

To a solution of 2,4-dichloropyrimidine (149 mg, 1 mmol) in THF (5 mL), tetrakis(triphenylphosphine) palladium (23 mg, 2 mol %) and 0.5M solution of phenylzinc bromide (2.1 mL, 1.05 mmol) in THF were added. The reaction mixture was stirred at 50° C. for overnight. Then it was added saturated ammonium chloride solution and extracted with EtOAc twice. The organic layers were combined, washed with water and dried (MgSO4). Evaporation of solvent gave a yellow residue which was purified by Prep. HPLC to afford a yellowish oil as 2-chloro-4-phenyl-pyrimidine to carry on.

後処理

  1. extractionextracted with EtOAc twice
  2. washwashed with water
  3. dry with materialdried (MgSO4)
  4. customEvaporation of solvent
  5. customgave a yellow residue which
  6. customwas purified by Prep

出典と根拠

ORDレコード
ord-c66e1f1e115741c89844e9fcbc4c3e59
出典データセット
uspto-grants-2016_01
特許番号
US09227940B2

関連ノート

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