TBAF tetrahydrofuran → (S)-N2-[1-(4-fluorophenyl)ethyl]-6-(oxazol-5-yl)-N4-(pyrazin-2-yl)pyrimidine-2,4-diamine

HRID 1187687ノート

反応式

HRID 1187687 の反応式
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([NH:10][C:11]2[N:16]=[C:15]([NH:17][C:18]3[CH:23]=[N:22][CH:21]=[CH:20][N:19]=3)[CH:14]=[C:13]([C:24]3[O:28][C:27]([Si](C(C)C)(C(C)C)C(C)C)=[N:26][CH:25]=3)[N:12]=2)[CH3:9])=[CH:4][CH:3]=1.O1CCCC1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1.C(OCC)(=O)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([NH:10][C:11]2[N:16]=[C:15]([NH:17][C:18]3[CH:23]=[N:22][CH:21]=[CH:20][N:19]=3)[CH:14]=[C:13]([C:24]3[O:28][CH:27]=[N:26][CH:25]=3)[N:12]=2)[CH3:9])=[CH:4][CH:3]=1

参加物

5

反応物 2

HCID 11078149TBAF tetrahydrofuranHCID 86659385(S)-N2-[1-(4-fluorophenyl)ethyl]-N4-(pyrazin-2-yl)-6-[2-(triisopropylsilyl)oxazol-5-yl]pyrimidine-2,4-diamine

生成物 1

HCID 56599390(S)-N2-[1-(4-fluorophenyl)ethyl]-6-(oxazol-5-yl)-N4-(pyrazin-2-yl)pyrimidine-2,4-diamine収率 69.6%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

122 mg of (S)—N2-[1-(4-fluorophenyl)ethyl]-N4-(pyrazin-2-yl)-6-[2-(triisopropylsilyl)oxazol-5-yl]pyrimidine-2,4-diamine was dissolved in 1.2 ml of tetrahydrofuran, and 0.5 ml of 1 M tetrabutylammonium fluoride tetrahydrofuran solution was added. The reaction solution was stirred at room temperature for 20 min, and then diluted with ethyl acetate. The solution was washed in turn with water and brine and then dried over magnesium sulfate. The solvent was distilled off under reduced pressure, and then the obtained residue was purified by silica gel column chromatography to obtain 60 mg of (S)—N2-[1-(4-fluorophenyl)ethyl]-6-(oxazol-5-yl)-N4-(pyrazin-2-yl)pyrimidine-2,4-diamine as white powder. The obtained compound was subjected to hydrochlorination using a conventional method to obtain 45 mg of the objective compound as pale orange powder.

後処理

  1. washThe solution was washed in turn with water and brine
  2. dry with materialdried over magnesium sulfate
  3. distillationThe solvent was distilled off under reduced pressure
  4. customthe obtained residue was purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-524a4789ad874731bd5e415214cf38f6
出典データセット
uspto-grants-2014_03
特許番号
US08673891B2

反応ノート

読み込み中…