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

HRID 1269623노트

반응식

HRID 1269623 반응식
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

참가 물질

7

반응물 3

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

생성물 1

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

시약·촉매·용매 3

HCID 11979704Tetrakis(triphenylphosphine)palladium촉매HCID 962Water용매HCID 80711,2-Dimethoxyethane용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-9d97af0c884f4b7d818c912070e2bdbe
출처 데이터셋
uspto-grants-2007_04
특허 번호
US07199239B2

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