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Pyridine → HCID 23020506, compound

HRID 1373016
Notes
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Reaction equation

HRID 1373016 reaction equation
[NH2:1][C:2]1[N:7]([CH3:8])[C:6](=[O:9])[C:5]([C:10]2[CH:15]=[CH:14][C:13](=[O:16])[NH:12][CH:11]=2)=[C:4]([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([F:23])[CH:18]=2)[N:3]=1.[C:24]1(B(O)O)[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.N1C=CC=CC=1>C([O-])(=O)C.[Cu+2].C([O-])(=O)C.CN(C)C=O>[NH2:1][C:2]1[N:7]([CH3:8])[C:6](=[O:9])[C:5]([C:10]2[CH:15]=[CH:14][C:13](=[O:16])[N:12]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[CH:11]=2)=[C:4]([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([F:23])[CH:18]=2)[N:3]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 1049PyridineHCID 66827Phenylboronic AcidHCID 23020487HCID 23020487, compound

Product 1

HCID 23020506HCID 23020506, compoundYield 31.7%

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalyst
HCID 6228
Dimethylformamide
Solvent

Procedure

In a flask were placed 2-amino-6-(3-fluorophenyl)-3-methyl-5-(6-oxo-1,6-dihydro-3-pyridinyl)-3,4-dihydro-4-pyrimidinone (40 mg, 0.13 mmol), copper acetate (3 mg, 0.01 mmol), phenylboronic acid (31 mg, 0.26 mmol), pyridine (21 μL, 0.26 mmol) and N,N-dimethylformamide (2 mL), followed by stirring at room temperature for 24 hour. After filtering off the insoluble matters, the filtrate was purified by HPLC, to give the title compound (16 mg). MS m/e (ESI) 389 (MH+).

Workup

  1. customIn a flask were placed
  2. filtrationAfter filtering off the insoluble matters
  3. customthe filtrate was purified by HPLC

Sources & evidence

ORD record
ord-5b0d05cb70954604b8ebddb85f7b0b1b
Source dataset
uspto-grants-2007_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07160892B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes