2,4-DICHLORO-5H-PYRROLO[3,2-D]PYRIMIDINE Chemical Properties

Melting point:

226-228 °C(Solv: water (7732-18-5); methanol (67-56-1))

Boiling point:

306.2±24.0 °C(Predicted)

Density 

1.675±0.06 g/cm3(Predicted)

storage temp. 

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

pka

10.67±0.40(Predicted)

Appearance

White to yellow Solid

InChI

InChI=1S/C6H3Cl2N3/c7-5-4-3(1-2-9-4)10-6(8)11-5/h1-2,9H

InChIKey

MVTLFDKTYGKJEX-UHFFFAOYSA-N

SMILES

C1(Cl)=NC(Cl)=C2NC=CC2=N1

Safety Information

HazardClass 

IRRITANT

HS Code 

2933599590

2,4-DICHLORO-5H-PYRROLO[3,2-D]PYRIMIDINE Usage And Synthesis

Uses

2,4-Dichloro-5H-pyrrolo[3,2-d]pyrimidine is an organic intermediate. It can be used to prepare a pyrrolo[3,2-d]pyrimidinone analogue, which is a potent DPP-IV inhibitor that is able to effectively lower blood glucose without causing risks such as weight gain and hypoglycaemia, and achieve prolonged therapeutic control of blood glucose.

Synthesis

1H-pyrrolo[3,2-d]pyrimidine-2,4(3H,5H)-dione (0.38 g, 2.52 mmol) was used as starting material and suspended in phosphorus trichloride (30 mL). The suspension was heated to 120°C and the reaction was carried out for 6 h, during which the mixture gradually changed to a clarified homogeneous solution. Upon completion of the reaction, the mixture was cooled to room temperature and the excess phosphorus trichloride was subsequently removed under vacuum. The residue was cooled in an ice bath and cold ammonium hydroxide solution (30 mL, pH = 8) was slowly added and stirred under this condition for 30 minutes. At the end of the reaction, the precipitate was collected by filtration and washed with cold water. Finally, the resulting solid was dried under vacuum to afford the target product 2,4-dichloro-5H-pyrrolo[3,2-d]pyrimidine (0.33 g, 70% yield).

References

[1] Journal of Heterocyclic Chemistry, 1987, vol. 24, p. 821 - 827
[2] Patent: WO2009/62258, 2009, A1. Location in patent: Page/Page column 98
[3] Bioorganic and Medicinal Chemistry, 2014, vol. 22, # 7, p. 2113 - 2122
[4] Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 15, p. 4354 - 4363
[5] Patent: US2016/257696, 2016, A1. Location in patent: Paragraph 0069-0070

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