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Potassium Carbonate → 2,3-Dip-tolyl-7,8-dihydropyrido[2,3-b]pyrazin-6(5H)-one

HRID 406222
Notes
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Reaction equation

HRID 406222 reaction equation
Br[C:2]1[N:3]=[C:4]2[CH2:12][CH2:11][C:10](=[O:13])[NH:9][C:5]2=[N:6][C:7]=1Cl.B(O)(O)[C:15]1[CH:16]=[CH:17][C:18]([CH3:21])=[CH:19][CH:20]=1.C([O-])([O-])=O.[K+].[K+]>CC#N.O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[C:18]1([CH3:21])[CH:17]=[CH:16][C:15]([C:2]2[N:3]=[C:4]3[CH2:12][CH2:11][C:10](=[O:13])[NH:9][C:5]3=[N:6][C:7]=2[C:15]2[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=2)=[CH:20][CH:19]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 79799Tolylboronic acidHCID 866818522-bromo-3-chloro-7,8-dihydropyrido[2,3-b]pyrazin-6(5H)-one2×

Product 1

HCID 666655132,3-Dip-tolyl-7,8-dihydropyrido[2,3-b]pyrazin-6(5H)-one

Reagents, catalysts & solvents 3

HCID 178418476HCID 178418476, compound
Catalyst
HCID 962WaterSolvent
HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

To a stirrred suspension of 2-bromo-3-chloro-7,8-dihydropyrido[2,3-b]pyrazin-6(5H)-one (Intermediate J) (10 g, 38.1 mmol), p-tolylboronic acid (11.39 g, 84 mmol) in MeCN (400 ml) and water (100 ml) under N2 supply, was added solid K2CO3 (fine mesh) (7.90 g, 57.1 mmol) followed by Pd(PPh3)2Cl2 (1.337 g, 1.905 mmol). The yellow RM was heated to 80° C. and was left stirring for 66 hours. The RM was allowed to cool slowly to RT and then placed in the fridge for 3-4 hours. The fine yellow needles were filtered off under suction and were washed with small quantity of acetonitrile, followed by water. After air drying for 10 min, the solid was transferred, dried in vacuo at 40° C. for 2 hours, to afford the title compound as fine crystalline needles;

Workup

  1. waitwas left
  2. temperatureto cool slowly to RT
  3. waitplaced in the fridge for 3-4 hours
  4. filtrationThe fine yellow needles were filtered off under suction
  5. washwere washed with small quantity of acetonitrile
  6. customAfter air drying for 10 min
  7. customdried in vacuo at 40° C. for 2 hours

Sources & evidence

ORD record
ord-d37fa80646be4bd0a39252b6dc636bfa
Source dataset
uspto-grants-2014_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08754085B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes