Pyridine → HCID 135682056, compound

HRID 1791273Notes

Reaction equation

HRID 1791273 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([C:8]2[C:13]([Cl:14])=[CH:12][CH:11]=[CH:10][N:9]=2)[CH:5]=[CH:4][C:3]=1[C:15]([NH2:17])=[O:16].N1C=CC=CC=1.[CH3:24][O:25][CH2:26][C:27](Cl)=O.[OH-].[Na+]>C1COCC1>[Cl:14][C:13]1[C:8]([C:6]2[CH:5]=[CH:4][C:3]3[C:15](=[O:16])[NH:17][C:27]([CH2:26][O:25][CH3:24])=[N:1][C:2]=3[N:7]=2)=[N:9][CH:10]=[CH:11][CH:12]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 14798Sodium HydroxideHCID 96623Methoxyacetyl chlorideHCID 23537069HCID 23537069, compound

Product 1

HCID 135682056HCID 135682056, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Dissolve 6-amino-3′-chloro-[2,2′]bipyridinyl-5-carboxylic acid amide (0.5 g, 2.02 mmol) in anhydrous THF (10 mL) under N2 atmosphere. Add drop wise pyridine (0.36 g, 4.04 mmol) and methoxyacetyl chloride (0.48 g, 4.04 mmol) to the reaction mixture and stir at room temperature overnight. Add 10% aq. NaOH (10 mL) and reflux for 4 hours. Concentrate in vacuum, adjust the pH to 6.0 using AcOH, collect the solid by filtration and dry under vacuum to give 7-(3-chloro-pyridin-2-yl)-2-methoxymethyl-3H-pyrido[2,3-d]pyrimidin-4-one as a white solid.

Workup

  1. temperaturereflux for 4 hours
  2. concentrationConcentrate in vacuum
  3. customcollect the solid
  4. filtrationby filtration
  5. customdry under vacuum

Sources & evidence

ORD record
ord-0ceca5cd1c6a4e9aa6e737c0719f58ab
Source dataset
uspto-grants-2006_07
Patent number
US07074799B2

Reaction notes

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