Sodium Carbonate → 2-Methylsulfanyl-4-(4-trifluoromethylphenyl)pyrimidine

HRID 1269623ノート

反応式

HRID 1269623 の反応式
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([S:8][CH3:9])[N:3]=1.C(=O)([O-])[O-].[Na+].[Na+].[F:16][C:17]([F:28])([F:27])[C:18]1[CH:23]=[CH:22][C:21](B(O)O)=[CH:20][CH:19]=1>C(COC)OC.O.[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>[CH3:9][S:8][C:4]1[N:3]=[C:2]([C:21]2[CH:22]=[CH:23][C:18]([C:17]([F:28])([F:27])[F:16])=[CH:19][CH:20]=2)[CH:7]=[CH:6][N:5]=1

参加物

7

反応物 3

HCID 10340Sodium CarbonateHCID 971134-Chloro-2-methylthiopyrimidineHCID 27343894-(Trifluoromethyl)phenylboronic acid

生成物 1

HCID 184483552-Methylsulfanyl-4-(4-trifluoromethylphenyl)pyrimidine

試薬・触媒・溶媒 3

HCID 11979704Tetrakis(triphenylphosphine)palladium触媒HCID 962Water溶媒HCID 80711,2-Dimethoxyethane溶媒

実験手順

To a solution of 4-chloro-2-methylthiopyrimidine (2.17 mL, 18.7 mmol) in dimethoxyethane (140 mL) and water (70 mL) was added sodium carbonate (5.15 g, 48.5 mmol), 4-trifluoromethylphenylboronic acid and tetrakis(triphenylphosphine) palladium (0) (0.43 g). The resulting mixture was heated at reflux under nitrogen for 18 h, then allowed to cool to room temperature and the dimethoxyethane removed in vacuo. The residue was diluted with water (30 mL) and extracted CH2Cl2 (2×100 mL). The organic solution was dried (MgSO4) and the solvents removed in vacuo. Purification by Biotage™ chromatography (Silica, 90 g) eluting 19:1 cyclohexane:EtOAc yielded the title compound as a pale yellow solid (4.47 g).

後処理

  1. temperatureThe resulting mixture was heated
  2. temperatureat reflux under nitrogen for 18 h
  3. customthe dimethoxyethane removed in vacuo
  4. additionThe residue was diluted with water (30 mL)
  5. extractionextracted CH2Cl2 (2×100 mL)
  6. dry with materialThe organic solution was dried (MgSO4)
  7. customthe solvents removed in vacuo
  8. customPurification by Biotage™ chromatography (Silica, 90 g)
  9. washeluting 19:1 cyclohexane

出典と根拠

ORDレコード
ord-9d97af0c884f4b7d818c912070e2bdbe
出典データセット
uspto-grants-2007_04
特許番号
US07199239B2

反応ノート

読み込み中…