5-(4-AMINO-2-FLUOROPHENYLAMINO)-8-METHYLPYRIDO[2,3-D]PYRIMIDINE-4,7(3H,8H)-DIONE synthesis

5synthesis methods

Product Name:5-(4-AMINO-2-FLUOROPHENYLAMINO)-8-METHYLPYRIDO[2,3-D]PYRIMIDINE-4,7(3H,8H)-DIONE
CAS Number:1035556-26-3
Molecular formula:C14H12FN5O2
Molecular Weight:301.28

3-BENZYL-5-(2-FLUORO-4-NITROPHENYLAMINO)-8-METHYLPYRIDO[2,3-D]PYRIMIDINE-4,7(3H,8H)-DIONE

1035556-25-2
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5-(4-AMINO-2-FLUOROPHENYLAMINO)-8-METHYLPYRIDO[2,3-D]PYRIMIDINE-4,7(3H,8H)-DIONE

1035556-26-3
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Yield:1035556-26-3 65%

Reaction Conditions:

with ammonium formate;palladium hydroxide on carbon in 1,4-dioxane at 90; for 4 h;

Steps:

5

5-(4-Amino-2-fluorophenylamino)-8-methylpyrido [2,3-d] pyrimidine- 4,7(3H,8H)-dione (compound 5E): 3-Benzyl-5-(2-fluoro-4-nitrophenylamino)-8- methylpyrido[2,3- d]pyrimidine-4,7(3H,8H)-dione (900 mg, 2.1 mmol), palladium hydroxide (20% on carbon, 500 mg) and ammonium formate (500 mg, 7.9 3 mmol, 3.7 eq) were stirred in dioxane (10 mL) at 90 ⁰C for 4 hours. The suspension was filtered and the solid refluxed in DMF (20 mL) for 1 hour then filtered. This was repeated 3 times. The filtrates were combined and evaporated to give 420 mg of title compound as a white solid (65%). ¹H NMR (400 MHz, MeOD) δ ppm 3.56 (br. s., 3 H) 5.38 (s, 1 H) 6.51 (s, 1 H) 6.54 (t, J=I.89 Hz, 1 H) 7.07 (t, J=8.46 Hz, 1 H) 8.17 (s, 1 H) [M+H] calc'd for Ci₄Hi₂FN₅O₂, 302; found, 302.

References:

WO2008/79814,2008,A2 Location in patent:Page/Page column 107-108

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References

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References

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3-Benzyl-5-hydroxy-8-methyl-3H,8H-pyrido[2,3-d]pyrimidine-4,7-dione

1035556-23-0
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References

3-Benzyl-5-chloro-8-methyl-3H,8H-pyrido[2,3-d]pyrimidine-4,7-dione

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References

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5-(4-AMINO-2-FLUOROPHENYLAMINO)-8-METHYLPYRIDO[2,3-D]PYRIMIDINE-4,7(3H,8H)-DIONE synthesis