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

HRID 717107
Notes
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Reaction equation

HRID 717107 reaction equation
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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

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

Procedure

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%).

Workup

  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

Sources & evidence

ORD record
ord-de066c1b8c37473ba4b475aa69aa2024
Source dataset
uspto-grants-2015_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09193689B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes