2,4,7-Trichloropyrido[2,3-d]pyrimidine Chemical Properties

Boiling point:

316.4±42.0 °C(Predicted)

Density 

1.685±0.06 g/cm3(Predicted)

storage temp. 

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

pka

-2.53±0.30(Predicted)

Appearance

White to off-white Solid

InChI

InChI=1S/C7H2Cl3N3/c8-4-2-1-3-5(9)12-7(10)13-6(3)11-4/h1-2H

InChIKey

DNFDLCRLLQVUQK-UHFFFAOYSA-N

SMILES

C1(Cl)=NC(Cl)=C2C=CC(Cl)=NC2=N1

Safety Information

Hazard Codes 

T

Risk Statements 

25-41

Safety Statements 

26-39-45

RIDADR 

UN 2811 6.1 / PGIII

WGK Germany 

3

HS Code 

2933998090

2,4,7-Trichloropyrido[2,3-d]pyrimidine Usage And Synthesis

Uses

2,4,7-Trichloropyrido[2,3-d]pyrimidine is used in the synthetic preparation of dual mTORC1/mTORC2 inhibitors and the discovery of AZD8055 and AZD2014 as potential antitumor agents.

Synthesis

The general procedure for the synthesis of 2,4,7-trichloropyrido[2,3-d]pyrimidine (Inter.5) using 7-chloropyrido[2,3-d]pyrimidine-2,4(1H,3H)-dione (Inter.4) as a starting material is as follows: To a stirred anhydrous toluene suspension of 0.5 M Inter.4 (1 equiv.) in an inert atmosphere was slowly added diisopropylethylamine (3 equivalent). The reaction mixture was heated to 70 °C and maintained for 30 min and subsequently cooled to room temperature. Next, phosphorous oxychloride (POCl3, 3 eq.) was added and the reaction mixture was heated to 100 °C for 2.5 hours. Upon completion of the reaction, the mixture was cooled and concentrated under vacuum to give a crude product slurry. The crude product was suspended in ethyl acetate (EtOAc) and filtered through a thin diatomaceous earth pad. The filtrate was concentrated under vacuum to give a brown oil. The oily substance was dissolved in dichloromethane (CH2Cl2) and stirred on silica gel for 30 minutes. Afterwards, the silica gel was removed by filtration and the filtrate was concentrated. The crude product was purified by fast chromatography (silica gel, SiO2) to afford analytically pure 2,4,7-trichloropyrido[2,3-d]pyrimidine (48% yield, 96% purity). Mass spectrometry (LC-MS, ESP) analysis resulted in: m/z 234 [M + H]+, retention time (R/T) = 4.21 min.

References

[1] Patent: WO2007/60404, 2007, A1. Location in patent: Page/Page column 57; 59
[2] Patent: WO2008/23161, 2008, A1. Location in patent: Page/Page column 101
[3] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 5, p. 1212 - 1216
[4] Patent: WO2008/23161, 2008, A1. Location in patent: Page/Page column 102-103
[5] Patent: CN102887895, 2016, B. Location in patent: Paragraph 0310; 0313; 0314

2,4,7-Trichloropyrido[2,3-d]pyrimidine(938443-20-0)Related Product Information

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