Ammonia → (5-Amino-6-ethoxy-pyridin-3-yl)-(7-isopropyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-methanone

HRID 82269

反応式

HRID 82269 の反応式
Br[C:2]1[CH:3]=[C:4]([C:11]([C:13]2[C:21]3[CH:20]=[N:19][CH:18]=[N:17][C:16]=3[N:15]([CH:22]([CH3:24])[CH3:23])[CH:14]=2)=[O:12])[CH:5]=[N:6][C:7]=1[O:8][CH2:9][CH3:10].[NH3:25]>CN1C(=O)CCC1.O.[Cu-]=O>[NH2:25][C:2]1[CH:3]=[C:4]([C:11]([C:13]2[C:21]3[CH:20]=[N:19][CH:18]=[N:17][C:16]=3[N:15]([CH:22]([CH3:24])[CH3:23])[CH:14]=2)=[O:12])[CH:5]=[N:6][C:7]=1[O:8][CH2:9][CH3:10]

参加物

6

反応物 2

HCID 222AmmoniaHCID 70817466(5-Bromo-6-ethoxy-pyridin-3-yl)-(7-isopropyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-methanone

生成物 1

HCID 70817179(5-Amino-6-ethoxy-pyridin-3-yl)-(7-isopropyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-methanone収率 24%

試薬・触媒・溶媒 3

HCID 178419072HCID 178419072、化合物触媒HCID 962Water溶媒HCID 13387N-methyl-2-pyrrolidone溶媒

反応条件

温度
130 °C

実験手順

Copper(I) oxide (38.6 mg, 0.27 mmol) was added to (5-Bromo-6-ethoxy-pyridin3-yl)-(7-isopropyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-methanone (Preparation 241, 350 mg, 0.89 mmol) in concentrated ammonia solution (6 mL) and NMP (1 mL). The mixture was heated in a sealed vessel at 130° C. for 17 hours. The reaction mixture was cooled to room temperature and diluted with water (10 ml). It was extracted with 20% i-PrOH in DCM (6×50 mL), dried (Na2SO4) and evaporated in vacuo. The crude material was purified by column chromatography on silica gel (MeOH:DCM 5:95) to afford the title compound as a yellow solid in 24% yield, 70 mg. LCMS (system 10): Rt=2.99 min; m/z 326 [M+H]+.

後処理

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionIt was extracted with 20% i-PrOH in DCM (6×50 mL)
  3. dry with materialdried (Na2SO4)
  4. customevaporated in vacuo
  5. customThe crude material was purified by column chromatography on silica gel (MeOH:DCM 5:95)

出典と根拠

ORDレコード
ord-eff853080e584be8a634d9ed7d3626ba
出典データセット
uspto-grants-2014_09
特許番号
US08846698B2

関連ノート

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