Sulfuric Acid → 5-Chloro-6-fluoro-8-methylpyrido[2,3-d]pyrimidine-4,7(3H,8H)-dione

HRID 2090556Notes

Reaction equation

[NH2:1][C:2]1(C#N)[CH2:7][C:6]([Cl:8])=[C:5]([F:9])[C:4](=[O:10])[N:3]1[CH3:11].S(=O)(=O)(O)O>C(O)=O>[Cl:8][C:6]1[C:7]2[C:4](=[O:10])[NH:3][CH:2]=[N:1][C:2]=2[N:3]([CH3:11])[C:4](=[O:10])[C:5]=1[F:9]

Participants

Conditions

Temperature: 80 °C

Procedure

Combine 2-amino-5-fluoro-4-chloro-1-methyl-6-oxo-1,6-dihydropyridine-carbonitrile (4.97 g, 246 mmol) and 99% formic acid (40 mL, 8 volumes) in a dried vessel. Heat to 80° C. When a solution is formed add aqueous 9 N sulfuric acid (25 mL, 5 volumes). After 20 hours, cool ambient temperature and add ice-water (50 mL, 10 volumes) with stirring. Cool in an ice bath to give a solid. After 30 minutes, collect the solid by filtration, rinse with water (2×5 mL), and dry in vacuo to give the title compound.

Workup

customWhen a solution is formed
temperaturecool ambient temperature
temperatureCool in an ice bath
customto give a solid
waitAfter 30 minutes
customcollect the solid
filtrationby filtration
washrinse with water (2×5 mL)
customdry in vacuo

Sources & evidence

ORD record: ord-482aa93b92e6415bad3c7fa8da7b329a
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08436200B2

Reaction notes

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