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

HRID 1356040

反応式

HRID 1356040 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-c1124d3b428a4405b0959df459e0a374
出典データセット
uspto-grants-2003_07
特許番号
US06586441B2

関連ノート

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