Potassium Carbonate → 2-Amino-4-(4-fluoro-phenyl)-6-methylsulfanyl-pyrimidine-5-carbonitrile

HRID 1356040

반응식

HRID 1356040 반응식
[NH2:1][C:2]1[N:7]=[C:6](Cl)[C:5]([C:9]#[N:10])=[C:4]([S:11][CH3:12])[N:3]=1.[F:13][C:14]1[CH:19]=[CH:18][C:17](B(O)O)=[CH:16][CH:15]=1.C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1>[NH2:1][C:2]1[N:7]=[C:6]([C:17]2[CH:18]=[CH:19][C:14]([F:13])=[CH:15][CH:16]=2)[C:5]([C:9]#[N:10])=[C:4]([S:11][CH3:12])[N:3]=1

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 2856454-Fluorophenylboronic acidHCID 185072602-Amino-4-chloro-6-methylsulfanyl-pyrimidine-5-carbonitrile

생성물 1

HCID 185073312-Amino-4-(4-fluoro-phenyl)-6-methylsulfanyl-pyrimidine-5-carbonitrile수율 54%

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

To a stirred suspension of 0.50 g (2,49 mmol) 2-amino-4-chloro-6-methylsulfanyl-pyrimidine-5-carbonitrile in 10 ml toluene under argon at room temperature were added 384 mg (2.74 mmol)p-fluorobenzeneboronic acid, 288 mg (0.25 mmol) tetrakis(triphenyl-phosphine)palladium(O) and 638 mg (4.98 mmol) anhydrous potassium carbonate. The reaction mixture was heated at reflux for 16 h, then cooled to room temperature and partitioned between ethyl acetate and water. The organic phase was washed with brine, dried over sodium sulfate, and concentrated in vacuo. Chromatography (1/1 ethyl acetate/hexane) followed trituration in ether/hexane afforded 350 mg (54%) 2-amino-4-(4-fluoro-phenyl)-6-methylsulfanyl-pyrimidine-5-carbonitrile as a yellow crystalline solid. EI-MS m/e (%): 260 (M+, 37), 259 ([M—H]+, 100).

후처리

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 16 h
  3. custompartitioned between ethyl acetate and water
  4. washThe organic phase was washed with brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-c1124d3b428a4405b0959df459e0a374
출처 데이터셋
uspto-grants-2003_07
특허 번호
US06586441B2

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