Pyridine → 2-isobutoxymethyl-7-(3-trifluoromethyl-pyridin-2-yl)-3H-pyrido[2,3-d]pyrimidin-4-one

HRID 2054331Notes

Reaction equation

HRID 2054331 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([C:8]2[C:13]([C:14]([F:17])([F:16])[F:15])=[CH:12][CH:11]=[CH:10][N:9]=2)[CH:5]=[CH:4][C:3]=1[C:18]([NH2:20])=[O:19].N1C=CC=CC=1.[CH2:27]([O:31][CH2:32][C:33](Cl)=O)[CH:28]([CH3:30])[CH3:29].[OH-].[Na+]>C1COCC1>[CH2:27]([O:31][CH2:32][C:33]1[NH:20][C:18](=[O:19])[C:3]2[CH:4]=[CH:5][C:6]([C:8]3[C:13]([C:14]([F:17])([F:16])[F:15])=[CH:12][CH:11]=[CH:10][N:9]=3)=[N:7][C:2]=2[N:1]=1)[CH:28]([CH3:30])[CH3:29]

Participants

6

Reactant 4

HCID 1049PyridineHCID 14798Sodium HydroxideHCID 14146847Isobutoxyacetyl chlorideHCID 596557626-Amino-3'-trifluoromethyl-[2,2']bipyridinyl-5-carboxylic acid amide

Product 1

HCID 1360187452-isobutoxymethyl-7-(3-trifluoromethyl-pyridin-2-yl)-3H-pyrido[2,3-d]pyrimidin-4-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Dissolve 6-amino-3′-trifluoromethyl-[2,2′]bipyridinyl-5-carboxylic acid amide (0.5 g, 1.75 mmol) in anhydrous THF (25 mL) under N2 atmosphere. Add dropwise pyridine (0.325 mL, 4.0 mmol) and isobutoxyacetyl chloride (0.2 mL, 4.04 mmol) to the reaction mixture and stir at room temperature overnight. Add 10% aq. NaOH (10 mL) and stir at 50° C. for 4 hours. Concentrate in vacuum, adjust the pH to 6.0 using AcOH, collect the solid by filtration and purify by column chromatography to give 2-isobutoxymethyl-7-(3-trifluoromethyl-pyridin-2-yl)-3H-pyrido[2,3-d]pyrimidin-4-one as a white solid.

Workup

  1. stirringstir at 50° C. for 4 hours
  2. concentrationConcentrate in vacuum
  3. customcollect the solid
  4. filtrationby filtration
  5. custompurify by column chromatography

Sources & evidence

ORD record
ord-7b78f9291acf4801b716741215c7a1c0
Source dataset
uspto-grants-2008_02
Patent number
US07329664B2

Reaction notes

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