Cesium carbonate → 9-(Cyclopropylmethyl)-8-fluoro-9H-pyrido[4',3':4,5]pyrrolo[2,3-d]pyrimidin-2-amine

HRID 79148ノート

反応式

HRID 79148 の反応式
C1(P(C2C=CC=CC=2)C2C3OC4C(=CC=CC=4P(C4C=CC=CC=4)C4C=CC=CC=4)C(C)(C)C=3C=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+].Br[C:50]1[C:51]([F:68])=[N:52][CH:53]=[CH:54][C:55]=1[C:56]1[C:57]([NH:63][CH2:64][CH:65]2[CH2:67][CH2:66]2)=[N:58][C:59]([NH2:62])=[N:60][CH:61]=1>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH:65]1([CH2:64][N:63]2[C:57]3[N:58]=[C:59]([NH2:62])[N:60]=[CH:61][C:56]=3[C:55]3[CH:54]=[CH:53][N:52]=[C:51]([F:68])[C:50]2=3)[CH2:67][CH2:66]1

参加物

5

反応物 3

HCID 10796Cesium carbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 582995575-(3-Bromo-2-fluoropyridin-4-yl)-N4-(cyclopropylmethyl)pyrimidine-2,4-diamine

生成物 1

HCID 583000719-(Cyclopropylmethyl)-8-fluoro-9H-pyrido[4',3':4,5]pyrrolo[2,3-d]pyrimidin-2-amine収率 79%

試薬・触媒・溶媒 1

HCID 9811564Bis(dibenzylideneacetone)palladium触媒

反応条件

温度
100 °C

実験手順

To a vacuum to argon purged vial containing 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (0.017 g, 0.030 mmol), tris(dibenzylideneacetone)dipalladium (0) (0.014 g, 0.015 mmol), cesium carbonate (0.19 g, 0.59 mmol) and compound 240 (0.100 g, 0.30 mmol) was added degassed dioxane (2.00 mL). The reaction was stirred at 100° C. After 4 h, the reaction was cooled and applied directly to silica. Silica gel chromatography (gradient elution 40 to 90% ethyl acetate in hexanes) afforded compound 241 (0.060 g, 79% yield). 1H NMR (500 MHz, CDCl3) δ ppm 0.45-0.57 (m, 4 H) 1.34-1.47 (m, 1 H) 4.32 (d, J=7.09 Hz, 2 H) 5.46 (br. s., 2 H) 7.68 (dd, J=5.26, 2.81 Hz, 1 H) 8.02 (dd, J=5.13, 1.71 Hz, 1 H) 8.93 (s, 1 H).

後処理

  1. additionwas added
  2. customdegassed dioxane (2.00 mL)
  3. temperaturethe reaction was cooled
  4. washSilica gel chromatography (gradient elution 40 to 90% ethyl acetate in hexanes)

出典と根拠

ORDレコード
ord-e07c7a7fd13b4b65809915b6643ccacb
出典データセット
uspto-grants-2014_09
特許番号
US08841312B2

反応ノート

読み込み中…