SYNTHESIS OF 2-AMINO-4-CHLORO-6,9-BIS-(2,4-DIMETHOXYBENZYL)-6,7,8,9-TETRAHYDRO-5H-PYRIMIDO[4,5-e][1,4] DIAZEPINE: A POTENTIALLY USEFUL INTERMEDIATE TO PYRIMIDO-[4,5-e][1,4]DIAZEPINE-B ASED FOLATES

Practical and efficient methods have been developed for the synthesis of 4,6,8,9-tetrasubstituted 8,9-dihydro-5H-pyrimido[4,5-e][1,4]diazepin-7(6H)-ones from 4,6-dicholoropyrimidine aldehyde, N-substituted amino acid esters, and amines in five steps. This synthetic strategy is based on suitably substituted pyrimidines as bis-electrophilic species reacting with various amines to construct the pyrimido[4,5-e][1,4]diazepine core with a strategically anchored functional group for further derivatization. The utility of this methodology was demonstrated through the preparation of a 33-membered library of representative 8,9-dihydro-5H-pyrimido[4,5-e][1,4]diazepin-7(6H)-ones in good to excellent yields.

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One pot synthesis of cis-bispyrimidodiazepinone derivatives via low-valent titanium reagent (TiCl4/Sm)

Dou

Shi

2011

Org. Biomol. Chem.

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An efficient and convenient method for the preparation of cis-bispyrimidodiazepinone derivatives has been described. A variety of substrates can participate in the process with good yields, making this methodology suitable for library synthesis in drug discovery efforts. The mechanistic course of the reaction suggests the involvement of reduction, coupling which determine the products' configuration and cyclization by one-pot.

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SYNTHESIS OF 2-AMINO-4-CHLORO-6,9-BIS-(2,4-DIMETHOXYBENZYL)-6,7,8,9-TETRAHYDRO-5H-PYRIMIDO[4,5-e][1,4] DIAZEPINE: A POTENTIALLY USEFUL INTERMEDIATE TO PYRIMIDO-[4,5-e][1,4]DIAZEPINE-B ASED FOLATES

Abstract: Reaction of 2-amino-4,6-dichloro-5-chloromethylpyrimidine with N,W-bis-(2,4-dimethoxybenzyl)ethane-l,2-diamine gave the title compound 7 which is potentially a useful intermediate to pyrimido [4,5-e][l,4]diazepine-based folates 1.

Cited by 4 publications

References 5 publications

1,4-Diazepines

1,4-Diazepines

Synthesis of Novel 8,9-Dihydro-5H-pyrimido[4,5-e][1,4]diazepin-7(6H)-ones

One pot synthesis of cis-bispyrimidodiazepinone derivatives via low-valent titanium reagent (TiCl4/Sm)

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