4-Chloro-5-fluoro-7H-pyrrolo[2,3-d]-pyrimidine Chemical Properties

Density 

1.642±0.06 g/cm3(Predicted)

storage temp. 

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

pka

9.72±0.50(Predicted)

Appearance

Light yellow to brown Solid

InChI

InChI=1S/C6H3ClFN3/c7-5-4-3(8)1-9-6(4)11-2-10-5/h1-2H,(H,9,10,11)

InChIKey

OOBFPXOXHUBRDN-UHFFFAOYSA-N

SMILES

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

Safety Information

HazardClass 

IRRITANT

HS Code 

2933599590

4-Chloro-5-fluoro-7H-pyrrolo[2,3-d]-pyrimidine Usage And Synthesis

Synthesis

General procedure for the synthesis of 4-chloro-5-fluoro-7H-pyrrolo[2,3-d]pyrimidines from 5-bromo-4-chloro-7H-pyrrolo[2,3-d]pyrimidines: 5-bromo-4-chloro-7H-pyrrolo[2,3-d]pyrimidines (0.6 g, 2.60 mmol) were dissolved in 30 mL of dry tetrahydrofuran (THF) and cooled to -78 °C. 4.10 mL of n-butyllithium (nBuLi, 1.6 M solution in hexane) was added dropwise over 10 min. The reaction mixture was stirred at -78 °C for 20 min, followed by dropwise addition of N-fluorobenzenesulfonimide (NFSI, 3.38 mmol, 1.065 g, dissolved in 6.5 mL of anhydrous THF) over 15 min. The reaction mixture was slowly warmed to room temperature and stirred overnight. Upon completion of the reaction, the reaction was quenched by the addition of 2 mL of water, and then the mixture was evaporated to dryness. The crude product was partitioned between ethyl acetate (EtOAc, 40 mL) and saturated ammonium chloride solution (20 mL), and the aqueous layer was extracted with 20 mL EtOAc. The organic layers were combined, washed with 20 mL of water and subsequently dried over anhydrous magnesium sulfate (MgSO?). After filtration, the solvent was evaporated. The crude product was purified by silica gel column chromatography using 4% methanol/dichloromethane (MeOH/CH?Cl?) as eluent to afford 4-chloro-5-fluoro-7H-pyrrolo[2,3-d]pyrimidine (0.36 g, 71% yield).1H NMR (DMSO-d?) δ: 7.70 (s, 1H), 8.62 (s, 1H), 12.25 (s, 1H (NH).

References

[1] Patent: WO2004/11478, 2004, A2. Location in patent: Page 27
[2] Journal of Medicinal Chemistry, 2004, vol. 47, # 21, p. 5284 - 5297
[3] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 24, p. 7742 - 7747
[4] Patent: WO2015/143712, 2015, A1. Location in patent: Page/Page column 34; 35
[5] Patent: US2016/244475, 2016, A1. Location in patent: Paragraph 0310; 0313

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