ホームMCPワークベンチSkills
ホームワークベンチ通知マイページ
llms.txt · MCPガイドプライバシーポリシー · 利用規約 · サポートv1.8.0
  1. ホーム
  2. /反応

Dichloromethane → (S)-methyl 2-(4-(3-ethylureido)-2-fluorophenyl)-4-(3-methylmorpholino)-5H-pyrrolo[3,4-d]pyrimidine-6-(7H)-carboxylate

HRID 1626680
ノート
印刷プレビュー

反応式

HRID 1626680 の反応式
Cl[C:2]1[N:3]=[C:4]([N:15]2[CH2:20][CH2:19][O:18][CH2:17][C@@H:16]2[CH3:21])[C:5]2[CH2:10][N:9]([C:11]([O:13][CH3:14])=[O:12])[CH2:8][C:6]=2[N:7]=1.[CH2:22]([NH:24][C:25]([NH:27][C:28]1[CH:33]=[CH:32][C:31](B2OC(C)(C)C(C)(C)O2)=[C:30]([F:43])[CH:29]=1)=[O:26])[CH3:23].ClCCl.C(=O)([O-])[O-].[Na+].[Na+]>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].CCO.O.COCCOC>[CH2:22]([NH:24][C:25](=[O:26])[NH:27][C:28]1[CH:33]=[CH:32][C:31]([C:2]2[N:3]=[C:4]([N:15]3[CH2:20][CH2:19][O:18][CH2:17][C@@H:16]3[CH3:21])[C:5]3[CH2:10][N:9]([C:11]([O:13][CH3:14])=[O:12])[CH2:8][C:6]=3[N:7]=2)=[C:30]([F:43])[CH:29]=1)[CH3:23]
参加物実験手順後処理出典と根拠反応ノート

参加物

9

反応物 4

HCID 6344DichloromethaneHCID 10340Sodium CarbonateHCID 666787871-Ethyl-3-(3-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)urea2 回HCID 86663170(S)-methyl 2-chloro-4-(3-methylmorpholino)-5H-pyrrolo[3,4-d]pyrimidine-6(7H)-carboxylate2 回

生成物 1

HCID 66678967(S)-methyl 2-(4-(3-ethylureido)-2-fluorophenyl)-4-(3-methylmorpholino)-5H-pyrrolo[3,4-d]pyrimidine-6-(7H)-carboxylate
収率 4.2%

試薬・触媒・溶媒 4

HCID 44119782Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)触媒HCID 702Ethanol溶媒HCID 962Water溶媒HCID 80711,2-Dimethoxyethane溶媒

実験手順

A solution of (S)-methyl 2-chloro-4-(3-methylmorpholino)-5H-pyrrolo[3,4-d]pyrimidine-6(7H)-carboxylate (intermediate 26) (98 mg, 0.313 mmol), 1-ethyl-3-(3-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)urea (intermediate 28) (110 mg, 0.357 mmol), [1,1′-Bis(diphenylphosphino)ferrocene]dichloropalladium (II), complex with dichloromethane (13 mg, 0.0157 mmol) and sodium carbonate (93 mg, 0.876 mmol) in 2 ml of a 7:3:1 mixture of DME:H2O:EtOH respectively was heated in the microwave at 115° C. for 45 minutes. The reaction was concentrated in vacuo and the residue was re-dissolved in a mix of H2O and EtOAc. The aqueous phase was extracted into EtOAc and the organic extracts were combined and concentrated in vacuo. The sample was then purified via preparative HPLC at low pH and then triturated in MeOH and filtered to yield the title compound (6 mg, 4%).

後処理

  1. concentrationThe reaction was concentrated in vacuo
  2. dissolutionthe residue was re-dissolved in
  3. additiona mix of H2O and EtOAc
  4. extractionThe aqueous phase was extracted into EtOAc
  5. concentrationconcentrated in vacuo
  6. customThe sample was then purified via preparative HPLC at low pH
  7. customtriturated in MeOH
  8. filtrationfiltered

出典と根拠

ORDレコード
ord-2acafa66c7984fbba5a19901a92565d8
出典データセット
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08785457B2

反応ノート

読み込み中…

このページの内容参加物実験手順後処理出典と根拠反応ノート