6-Benzyl-4-chloro-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine Chemical Properties

Boiling point:

396.6±42.0 °C(Predicted)

Density 

1.273±0.06 g/cm3(Predicted)

storage temp. 

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

pka

5.01±0.20(Predicted)

Appearance

Light yellow to yellow Powder

InChI

InChI=1S/C14H14ClN3/c15-14-12-9-18(7-6-13(12)16-10-17-14)8-11-4-2-1-3-5-11/h1-5,10H,6-9H2

InChIKey

RPJAAZOTUXKSEV-UHFFFAOYSA-N

SMILES

C1=NC(Cl)=C2CN(CC3=CC=CC=C3)CCC2=N1

6-Benzyl-4-chloro-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine Usage And Synthesis

Uses

Pyridine [4,3-D]pyrimidine compounds are nitrogen-containing heterocyclic compounds with unique structures and functions, occupying a very important position in organic chemistry and becoming one of the hot topics in chemical research today. Pyridine [4,3-D]pyrimidine derivatives possess biological activities such as antibacterial, anticancer, anti-inflammatory, antidiabetic, and antiviral activity, and their synthesis has attracted much attention.

Synthesis

A mixture of 6-benzyl-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4(3H)-one (5.0 g, 0.02 mol), phosphoryl chloride(3.30 mL, 0.035 mol), acetonitrile (80 mL) and DMF (catalytic amount) was heated to at 70° C for 1 hour. The mixture was reduced in vacuo and the remaining black residue was taken up in dichloromethane (250 ml) and poured over ice. The mixture was carefully neutralized with the addition of solid sodium bicarbonate. The layers were separated and the organic dried over sodium sulfate and reduced in vacuo. The mixture was chromatographed using an ethyl acetate: hexanes gradient on an isco flash chromatography system. The combined pure fractions were reduced in vacuo to yield 6-Benzyl-4-chloro-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine as a yellow oil.

References

[1] Patent: US2006/258689, 2006, A1. Location in patent: Page/Page column 23; 28
[2] Patent: US2008/275037, 2008, A1. Location in patent: Page/Page column 23
[3] Patent: WO2008/123963, 2008, A1. Location in patent: Page/Page column 44
[4] Journal of Medicinal Chemistry, 2008, vol. 51, # 11, p. 3124 - 3132
[5] Patent: WO2011/103715, 2011, A1. Location in patent: Page/Page column 40

6-Benzyl-4-chloro-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine(914612-23-0)Related Product Information

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