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

Melting point:

249-251℃

Boiling point:

504.1±50.0 °C(Predicted)

Density 

1.386±0.06 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

solubility 

Chloroform (Slightly)

form 

Solid

pka

2.00±0.30(Predicted)

color 

Pale Yellow to Light Yellow

InChI

InChI=1S/C16H20Cl2N6/c17-15-20-12-11(13(21-15)23-7-3-1-4-8-23)19-16(18)22-14(12)24-9-5-2-6-10-24/h1-10H2

InChIKey

PCVJQTVUJJJSRQ-UHFFFAOYSA-N

SMILES

C1(Cl)=NC(N2CCCCC2)=C2N=C(Cl)N=C(N3CCCCC3)C2=N1

LogP

2

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

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

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