2,6-Dichloro-4,8-dipiperidinopyrimidino[5,4-d]pyrimidine

Chemical Properties

Beige Solid

Uses

An antitumor nucleoside pyrimido pyrimidine.

Synthesis

General procedure for the synthesis of 2,6-dichloro-4,8-dipiperidinosubstituted pyrimido[5,4-d]pyrimidines from hexahydropyridine and perchloropyrimido[5,4-d]pyrimidines: perchloropyrimido[5,4-d]pyrimidines (13.1 g, 48.9 mmol), piperidines, CuI (0.28 g, 1.5 mmol) and Cs2CO3 (16.0 g, 48.9 mmol) were added to a 250mL two-necked flask. 100 mL of nitrobenzene was added as reaction solvent and the reaction was carried out at 180°C for 16 h under nitrogen protection. After completion of the reaction, the nitrobenzene solvent was removed by distillation under reduced pressure. Purification by column chromatography using a solvent mixture of petroleum ether (PE) and dichloromethane (DCM) (6:1, v/v) gave 17.0 g of solid product in 95.0% yield and 99% selectivity.

References

[1] Patent: CN106946887, 2017, A. Location in patent: Paragraph 0035; 0036; 0037
[2] Journal of Medicinal Chemistry, 2004, vol. 47, # 20, p. 4905 - 4922
[3] Medicinal Chemistry Research, 1996, vol. 6, # 1, p. 61 - 67
[4] Journal of Medicinal Chemistry, 2007, vol. 50, # 16, p. 3906 - 3920
[5] Patent: CN108069972, 2018, A. Location in patent: Paragraph 0005; 0017