Butyl vinyl ether → 6-(4-Acetyl-phenyl)-5-(4-chloro-phenyl)-1-phenyl-1,5-dihydro-pyrazolo[3,4-d]pyrimidin-4-one

HRID 1693513ノート

反応式

HRID 1693513 の反応式
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]([C:24]3[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][CH:25]=3)[C:10](=[O:23])[C:11]3[CH:16]=[N:15][N:14]([C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=4)[C:12]=3[N:13]=2)=[CH:4][CH:3]=1.[CH2:31]([O:35][CH:36]=[CH2:37])[CH2:32][CH2:33][CH3:34].C1(P(C2C=CC=CC=2)CCCP(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.CC([O-])=O.CC([O-])=O.[Pd+2].O>[C:31]([C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]([C:24]3[CH:25]=[CH:26][C:27]([Cl:30])=[CH:28][CH:29]=3)[C:10](=[O:23])[C:11]3[CH:16]=[N:15][N:14]([C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=4)[C:12]=3[N:13]=2)=[CH:4][CH:3]=1)(=[O:35])[CH3:32].[CH2:31]([O:35][CH:36]=[CH:37][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:9]([C:24]3[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][CH:25]=3)[C:10](=[O:23])[C:11]3[CH:16]=[N:15][N:14]([C:17]4[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=4)[C:12]=3[N:13]=2)=[CH:6][CH:7]=1)[CH2:32][CH2:33][CH3:34]

参加物

9

反応物 4

HCID 8108Butyl vinyl etherHCID 11430Potassium CarbonateHCID 812191,3-Bis(diphenylphosphino)propaneHCID 20472026-(4-bromophenyl)-5-(4-chlorophenyl)-1-phenyl-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one

生成物 2

HCID 116765606-(4-Acetyl-phenyl)-5-(4-chloro-phenyl)-1-phenyl-1,5-dihydro-pyrazolo[3,4-d]pyrimidin-4-oneHCID 672814696-[4-(2-Butoxy-vinyl)-phenyl]-5-(4-chloro-phenyl)-1-phenyl-1,5-dihydro-pyrazolo[3,4-d]pyrimidin-4-one

試薬・触媒・溶媒 3

HCID 167845palladium(II) acetate触媒HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
100 °C

実験手順

To a reaction tube charged with 6-(4-bromo-phenyl)-5-(4-chloro-phenyl)-1-phenyl-1,5-dihydro-pyrazolo[3,4-d]pyrimidin-4-one (20 mg, 0.042 mmol), butylvinyl ether (21 mg, 0.21 mmol), Pd(OAc)2 (1.0 mg, 0.004 mmol), 1,3-bis(diphenylphosphino)propane (3.5 mg, 0.008 mmol) and K2CO3 (7 mg, 0.05 mmol) is added water (0.05 mL) in DMF (0.5 mL). The system is purged with N2, sealed and heated to 100° C. for 14 h. After cooling down to room temperature, the mixture is hydrolyzed by adding 1 mL of 1 N HCl for 30 min. The mixture is then treated with H2O (5 mL) and extracted with EtOAc (3×2 mL). The combined extracts is concentrated and purified by preparative LC/MS to provide the title compound 6-(4-acetyl-phenyl)-5-(4-chloro-phenyl)-1-phenyl-1,5-dihydro-pyrazolo[3,4-d]pyrimidin-4-one and 6-[4-(2-butoxy-vinyl)-phenyl]-5-(4-chloro-phenyl)-1-phenyl-1,5-dihydro-pyrazolo[3,4-d]pyrimidin-4-one (example 360) as a by product (ratio about 1:2). Example 86: HPLC-MS calculated for C25H17ClNO2 (M+1+): 441.1. Found: 441.1. Example 360: HPLC-MS calculated C29H25ClN4O2 (M+1+): 497.2. Found: 497.2.

後処理

  1. customThe system is purged with N2
  2. customsealed
  3. temperatureAfter cooling down to room temperature
  4. additionby adding 1 mL of 1 N HCl for 30 min
  5. additionThe mixture is then treated with H2O (5 mL)
  6. extractionextracted with EtOAc (3×2 mL)
  7. concentrationThe combined extracts is concentrated
  8. custompurified by preparative LC/MS

出典と根拠

ORDレコード
ord-fefe230070d94f8093ca0fa7ac7156a9
出典データセット
uspto-grants-2012_04
特許番号
US08158634B2

反応ノート

読み込み中…