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Synthesis of 2-arylamino substituted 5,6-dihydropyrido[2,3-d]pyrimidine-7(8H)-ones from arylguanidines.

Molecular diversity (2012-10-12)
Iñaki Galve, Raimon Puig de la Bellacasa, David Sánchez-García, Xavier Batllori, Jordi Teixidó, José I Borrell
ABSTRACT

A practical protocol was developed for the synthesis of 2-arylamino substituted 4-amino-5,6-dihydropyrido[2,3-d]pyrimidin-7(8H)-ones from α,β-unsaturated esters, malononitrile, and an aryl substituted guanidine via the corresponding 3-aryl-3,4,5,6- tetrahydropyrido[2,3-d]pyrimidin-7(8H)-ones. Such compounds are formed upon treatment of 2-methoxy-6-oxo-1,4,5,6-tetrahydropyridine-3-carbonitriles with an aryl substituted guanidine in 1,4-dioxane and are converted to the desired 4-aminopyridopyrimidines with NaOMe/MeOH through a Dimroth rearrangement. The overall yields of this three-step protocol are, generally speaking, higher than the multicomponent reaction, previously developed by our group, between an α,β-unsaturated ester, malononitrile, and an aryl substituted guanidine.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
1,4-Dioxane, anhydrous, 99.8%
Sigma-Aldrich
1,4-Dioxane, ACS reagent, ≥99.0%
Sigma-Aldrich
Malononitrile, ≥99%
Sigma-Aldrich
1,4-Dioxane, suitable for HPLC, ≥99.5%
Supelco
1,4-Dioxane, analytical standard
Sigma-Aldrich
1,4-Dioxane, ReagentPlus®, ≥99%
Supelco
1,4-Dioxane solution, certified reference material, 2000 μg/mL in methanol, ampule of 1 mL
Sigma-Aldrich
1,4-Dioxane, ACS reagent, ≥99.0%
Sigma-Aldrich
1,4-Dioxane, puriss. p.a., ACS reagent, reag. ISO, reag. Ph. Eur., ≥99.5% (GC)
Sigma-Aldrich
Malononitrile, Lonza quality, ≥99.0% (calculated, GC, KF)
Sigma-Aldrich
1,4-Dioxane solution, NMR reference standard, 40% in benzene-d6 (99.6 atom % D)
Sigma-Aldrich
1,4-Dioxane solution, NMR reference standard, 40% in benzene-d6 (99.6 atom % D), chromium(III) acetylacetonate 5 mg/mL, NMR tube size 5 mm × 8 in.
Sigma-Aldrich
1,4-Dioxane solution, NMR reference standard, 10 mM in D2O ("100%", 99.96 atom % D), NMR tube size 5 mm × 7 in.
Supelco
1,4-Dioxane solution, NMR reference standard, 40% in benzene-d6 (99.6 atom % D), NMR tube size 5 mm × 8 in.
Sigma-Aldrich
1,4-Dioxane solution, NMR reference standard, 40% in benzene-d6 (99.6 atom % D), NMR tube size 10 mm × 8 in.
Supelco
1,4-Dioxane solution, NMR reference standard, 5 mM in chloroform-d (99.8 atom % D), NMR tube size 3 mm × 8 in.
Supelco
1,4-Dioxane solution, NMR reference standard, 5 mM in benzene-d6 (99.6 atom % D), NMR tube size 3 mm × 8 in.
Sigma-Aldrich
1,4-Dioxane solution, NMR reference standard, 40% in benzene-d6 (99.6 atom % D), chromium(III) acetylacetonate 5 mg/mL, NMR tube size 3 mm × 8 in.
Supelco
1,4-Dioxane solution, NMR reference standard, 40% in benzene-d6 (99.6 atom % D), NMR tube size 3 mm × 8 in.