2,4-Dichloroquinazoline → HCID 58972436、化合物

HRID 2264405ノート

反応式

HRID 2264405 の反応式
[Br-].[S:2]1[CH:6]=[CH:5][N:4]=[C:3]1[Zn+].[Cl:8][C:9]1[N:18]=[C:17](Cl)[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:10]=1>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:8][C:9]1[N:18]=[C:17]([C:3]2[S:2][CH:6]=[CH:5][N:4]=2)[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:10]=1

参加物

5

反応物 2

HCID 2528862,4-DichloroquinazolineHCID 178419763HCID 178419763、化合物2 回

生成物 1

HCID 58972436HCID 58972436、化合物

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
110 °C

実験手順

To a 0.5 M solution of 2-thiazolyl zinc bromide in THF (12.1 mL, 6.03 mmol, 1.2 equiv; commercially available from Aldrich) under Ar was added 2,4-dichloro-quinazoline (1.0 g, 5.02 mmol, 1.0 equiv) and tetrakis(triphenylphosphine) palladium(0) (232.2 mg, 0.20 mmol, 0.04 equiv) and the reaction mixture heated by microwave irradiation to 110° C. After 30 min additional 2-thiazolyl zinc bromide in THF (12.1 mL, 6.03 mmol, 1.2 equiv) was added and the reaction mixture heated to 110° C. for another 30 min. The crude reaction mixture was concentrated by evaporation under reduced pressure and the residue purified by silica column chromatography using a MPLC system (CombiFlash Companion, Isco Inc.) eluting with a gradient of heptane/ethyl acetate providing 0.36 g (29%) of the title compound. MS (ISP): 248.3 [M+H]+.

後処理

  1. temperaturethe reaction mixture heated to 110° C. for another 30 min
  2. customThe crude reaction mixture
  3. concentrationwas concentrated by evaporation under reduced pressure
  4. customthe residue purified by silica column chromatography
  5. washeluting with a gradient of heptane/ethyl acetate providing 0.36 g (29%) of the title compound

出典と根拠

ORDレコード
ord-bc795c0175bc41e5929868efba6e2637
出典データセット
uspto-grants-2010_12
特許番号
US07855194B2

反応ノート

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