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Potassium Carbonate → 5-methyl-3-[2-(4-methyl-piperazin-1-yl)-pyrimidin-5-yl]-2H-isoquinolin-1-one

HRID 717107
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HRID 717107 반응식
Cl[C:2]1[NH:3][C:4](=[O:13])[C:5]2[C:10]([CH:11]=1)=[C:9]([CH3:12])[CH:8]=[CH:7][CH:6]=2.[CH3:14][N:15]1[CH2:20][CH2:19][N:18]([C:21]2[N:26]=[CH:25][C:24](B3OC(C)(C)C(C)(C)O3)=[CH:23][N:22]=2)[CH2:17][CH2:16]1.C([O-])([O-])=O.[K+].[K+]>COCCOC.CCO.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]>[CH3:12][C:9]1[CH:8]=[CH:7][CH:6]=[C:5]2[C:10]=1[CH:11]=[C:2]([C:24]1[CH:23]=[N:22][C:21]([N:18]3[CH2:19][CH2:20][N:15]([CH3:14])[CH2:16][CH2:17]3)=[N:26][CH:25]=1)[NH:3][C:4]2=[O:13]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

HCID 11430Potassium CarbonateHCID 164142282-(4-Methylpiperazino)pyrimidine-5-boronic acid pinacol esterHCID 229310333-Chloro-5-methyl-2H-isoquinolin-1-one

생성물 1

HCID 717361125-methyl-3-[2-(4-methyl-piperazin-1-yl)-pyrimidin-5-yl]-2H-isoquinolin-1-one수율 32.1%

시약·촉매·용매 2

HCID 44119782
Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)
촉매
HCID 86587095Dimethoxyethane ethanol water용매

실험 절차

3-Chloro-5-methyl-2H-isoquinolin-1-one (50 mg, 0.26 mmol), 2-(4-methylpiperazin-1-yl)pyrimidine-5-boronic acid pinacol ester (118 mg, 0.39 mmol), K2CO3 (73 mg, 0.52 mmol) and Pd(dppf)Cl2 (10 mg, 0.013 mmol) in DME/EtOH/H2O 4:0.5:1 (2.75 mL) were added to a microwave vial and the reaction mixture purged with N2 for 10 min. The reaction mixture was irradiated using a microwave reactor (300 W, 100° C., 60 min). The reaction mixture was filtered through celite and concentrated in vacuo. The crude material was purified by silica gel column chromatography, eluting with CH2Cl2 and increasing the polarity to 50% MeOH/CH2Cl2. The crude material was trituared with MeOH and washed with isohexane to afford 5-methyl-3-[2-(4-methyl-piperazin-1-yl)-pyrimidin-5-yl]-2H-isoquinolin-1-one as an off-white solid (28 mg, 32%).

후처리

  1. customthe reaction mixture purged with N2 for 10 min
  2. customThe reaction mixture was irradiated
  3. custom(300 W, 100° C., 60 min)
  4. filtrationThe reaction mixture was filtered through celite and
  5. concentrationconcentrated in vacuo
  6. customThe crude material was purified by silica gel column chromatography
  7. washeluting with CH2Cl2
  8. temperatureincreasing the polarity to 50% MeOH/CH2Cl2
  9. washwashed with isohexane

출처 및 근거

ORD 기록
ord-de066c1b8c37473ba4b475aa69aa2024
출처 데이터셋
uspto-grants-2015_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09193689B2

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