Sodium Carbonate → HCID 69331478, compound

HRID 915059Notes

Reaction equation

HRID 915059 reaction equation
C([O-])([O-])=O.[Na+].[Na+].[NH2:7][C:8]1[N:9]=[C:10]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:11]([C:15]2[CH:16]=[CH:17][C:18](=[O:24])[N:19]([CH:21]([CH3:23])[CH3:22])[N:20]=2)=[N:12][C:13]=1Br.[C:31]1(B(O)O)[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>O.O1CCOCC1.CC(C)=O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[NH2:7][C:8]1[N:9]=[C:10]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:11]([C:15]2[CH:16]=[CH:17][C:18](=[O:24])[N:19]([CH:21]([CH3:23])[CH3:22])[N:20]=2)=[N:12][C:13]=1[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Participants

8

Reactant 3

HCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 866009156-(5-amino-6-bromo-3-phenyl-2-pyrazinyl)-2-isopropyl-3(2H)-pyridazinone

Product 1

HCID 69331478HCID 69331478, compoundYield 75.5%

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 180AcetoneSolventHCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent

Conditions

Temperature
102.5 °C

Procedure

Under nitrogen atmosphere, a solution of Na2CO3 (220 mg) in water (1.6 ml) was added to a suspension of 6-(5-amino-6-bromo-3-phenyl-2-pyrazinyl)-2-isopropyl-3(2H)-pyridazinone (200 mg), phenylboronic acid (158 mg) and tetrakis(triphenylphosphine)palladium (18 mg) in dioxane (6 ml) and the mixture was stirred at 100-105° C. for 2 hours. After addition of water (6 ml), a precipitate was collected by filtration and purified by column chromatography on silica gel eluting with a mixture of n-hexane and EtOAc (60:40 v/v) to give a solid. The solid was suspended in acetone and collected by filtration to give 6-(5-amino-3,6-diphenyl-2-pyrazinyl)-2-isopropyl-3(2H)-pyridazinone (150 mg).

Workup

  1. filtrationa precipitate was collected by filtration
  2. custompurified by column chromatography on silica gel eluting with a mixture of n-hexane and EtOAc (60:40 v/v)
  3. customto give a solid
  4. filtrationcollected by filtration

Sources & evidence

ORD record
ord-979f12e177184d03a9a77c82b4cb32c0
Source dataset
uspto-grants-2007_09
Patent number
US07265120B2

Reaction notes

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