2,4-DICHLORO-7H-PYRROLO2,3-DPYRIMIDINE Chemical Properties

Melting point:

247-250°C

Boiling point:

312.0±52.0 °C(Predicted)

Density 

1.79±0.1 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

Acetone (Slightly), DMSO (Slightly), Methanol (Slightly)

pka

9.18±0.20(Predicted)

form 

Solid

color 

Off-White to Yellow

Water Solubility 

Soluble in DMSO, ethyl acetate and methanol. Slightly soluble in water.

InChI

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

InChIKey

GHXBPCSSQOKKGB-UHFFFAOYSA-N

SMILES

C1(Cl)=NC(Cl)=C2C=CNC2=N1

Safety Information

Hazard Codes 

T

Risk Statements 

25-36-36/37/38-22

Safety Statements 

26-45-28-36

RIDADR 

UN2811

HazardClass 

IRRITANT

HS Code 

29335990

2,4-DICHLORO-7H-PYRROLO2,3-DPYRIMIDINE Usage And Synthesis

Chemical Properties

Crystalline Solid

Uses

It is used as a pharmaceutical intermediate.

Synthesis

General procedure for the synthesis of 2,4-dichloro-7H-pyrrolo[2,3-d]pyrimidines from 2,4-dihydroxypyrrolo[2,3-d]pyrimidines: 7H-pyrrolo[2,3-d]pyrimidine-2,4-diol (10.0 g, 66.2 mmol) and toluene (30 ml) were added to a reactor equipped with a stirrer. Phosphoryl chloride (18.5 ml, 198.5 mmol) was added slowly under stirring and the reaction system was subsequently warmed to 70 °C. Diisopropylethylamine (23.0 ml, 132.3 mmol) was added dropwise over 2.5 h to control the exothermic nature of the reaction. After the dropwise addition, the reaction temperature was raised to 106 °C and stirring was continued at this temperature for 16 hours. After completion of the reaction, the mixture was cooled to 25 °C and then slowly poured into a flask containing water (230 ml) and ethyl acetate (120 ml) and stirred overnight at room temperature. The reaction mixture was filtered through diatomaceous earth and then layered, the aqueous layer was extracted with ethyl acetate (3 x 75 ml). The organic layers were combined and washed with brine (100 ml). Darco KBB (1.24 g) was added to the organic layer, filtered again through diatomaceous earth and dried with anhydrous sodium sulfate (10.0 g). Finally, the solution was concentrated under reduced pressure to afford the target product 2,4-dichloro-7H-pyrrolo[2,3-d]pyrimidine in 52% yield.

References

[1] European Journal of Medicinal Chemistry, 2012, vol. 52, p. 205 - 212
[2] Patent: WO2007/12953, 2007, A2. Location in patent: Page/Page column 24
[3] Patent: US2010/3250, 2010, A1. Location in patent: Page/Page column 20
[4] Journal of Medicinal Chemistry, 2010, vol. 53, # 8, p. 3169 - 3182
[5] Patent: US2009/54425, 2009, A1. Location in patent: Page/Page column 21

2,4-DICHLORO-7H-PYRROLO2,3-DPYRIMIDINE(90213-66-4)Related Product Information

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