Cesium carbonate → (2S)-2-((6-(1-methyl-1H-pyrazol-4-yl)-1H-[1,2,3]triazolo[4,5-b]pyrazin-1-yl)methyl)-4-(5-(1-(2-(tetrahydro-2H-pyran-2-yloxy)ethyl)-1H-pyrazol-4-yl)pyrimidin-2-yl)morpholine

HRID 1478569ノート

反応式

HRID 1478569 の反応式
Br[C:2]1[CH:3]=[N:4][C:5]([N:8]2[CH2:13][CH2:12][O:11][C@H:10]([CH2:14][N:15]3[C:19]4=[N:20][C:21]([C:24]5[CH:25]=[N:26][N:27]([CH3:29])[CH:28]=5)=[CH:22][N:23]=[C:18]4[N:17]=[N:16]3)[CH2:9]2)=[N:6][CH:7]=1.[O:30]1[CH2:35][CH2:34][CH2:33][CH2:32][CH:31]1[O:36][CH2:37][CH2:38][N:39]1[CH:43]=[C:42](B2OC(C)(C)C(C)(C)O2)[CH:41]=[N:40]1.C(=O)([O-])[O-].[Cs+].[Cs+]>COCOC.O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH3:29][N:27]1[CH:28]=[C:24]([C:21]2[N:20]=[C:19]3[N:15]([CH2:14][C@H:10]4[O:11][CH2:12][CH2:13][N:8]([C:5]5[N:4]=[CH:3][C:2]([C:42]6[CH:41]=[N:40][N:39]([CH2:38][CH2:37][O:36][CH:31]7[CH2:32][CH2:33][CH2:34][CH2:35][O:30]7)[CH:43]=6)=[CH:7][N:6]=5)[CH2:9]4)[N:16]=[N:17][C:18]3=[N:23][CH:22]=2)[CH:25]=[N:26]1

参加物

7

反応物 3

HCID 10796Cesium carbonateHCID 593418191-[2-(oxan-2-yloxy)ethyl]-4-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 73507291HCID 73507291、化合物

生成物 1

HCID 118364842(2S)-2-((6-(1-methyl-1H-pyrazol-4-yl)-1H-[1,2,3]triazolo[4,5-b]pyrazin-1-yl)methyl)-4-(5-(1-(2-(tetrahydro-2H-pyran-2-yloxy)ethyl)-1H-pyrazol-4-yl)pyrimidin-2-yl)morpholine収率 77%

試薬・触媒・溶媒 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)触媒HCID 962Water溶媒HCID 8020Dimethoxymethane溶媒

反応条件

温度
80 °C

実験手順

(S)-4-(5-bromopyrimidin-2-yl)-2-((6-(1-methyl-1H-pyrazol-4-yl)-1H-[1,2,3]triazolo[4,5-b]pyrazin-1-yl)methyl)morpholine 300 mg (0.66 mmol) was dissolved in dimethoxymethane 12 ml, and 1-(2-(tetrahydro-2H-pyran-2-yloxy)ethyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)-1H-pyrazole 450 mg (1.39 mmol) was added. Cesium carbonate 641 mg (1.97 mmol) was dissolved in distilled water 3 ml, which was then added to the reaction solution. PdCl2(dppf)2 27 mg (0.03 mmol) was added, and the mixture was purged with N2 (g), followed by stirring at 80° C. for 4 hours. After the completion of the reaction, the reaction mixture was extracted with ethyl acetate and brine, and the organic layer was dried over Na2SO4. Prep LC with 5% MeOH/MC gave a product 290 mg (77%).

後処理

  1. additionwhich was then added to the reaction solution
  2. customthe mixture was purged with N2 (g)
  3. customAfter the completion of the reaction
  4. extractionthe reaction mixture was extracted with ethyl acetate and brine
  5. dry with materialthe organic layer was dried over Na2SO4

出典と根拠

ORDレコード
ord-e5b3321557a54708ab93aa6cc25abb6d
出典データセット
uspto-grants-2016_08
特許番号
US09403831B2

反応ノート

読み込み中…