Pyridine → HCID 135682056, compound

HRID 968628Notes

Reaction equation

HRID 968628 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-17f623db6c5d423bb487e4a0075d1f60
Source dataset
uspto-grants-2007_12
Patent number
US07304059B2

Reaction notes

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