4-Chloro-6-iodo-7-phenylsulfonyl-7H-pyrrolo[2,3-d]pyrimidine Chemical Properties

Boiling point:

564.2±60.0 °C(Predicted)

Density 

2.02±0.1 g/cm3(Predicted)

storage temp. 

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

form 

solid

pka

1.23±0.30(Predicted)

Appearance

Light yellow to yellow Solid

InChI

InChI=1S/C12H7ClIN3O2S/c13-11-9-6-10(14)17(12(9)16-7-15-11)20(18,19)8-4-2-1-3-5-8/h1-7H

InChIKey

PEVCDMDOTQHPPL-UHFFFAOYSA-N

SMILES

C1=NC(Cl)=C2C=C(I)N(S(C3=CC=CC=C3)(=O)=O)C2=N1

CAS DataBase Reference

876343-09-8

Safety Information

WGK Germany 

3

HS Code 

2933599590

Storage Class

11 - Combustible Solids

4-Chloro-6-iodo-7-phenylsulfonyl-7H-pyrrolo[2,3-d]pyrimidine Usage And Synthesis

Synthesis

General procedure for the synthesis of 4-chloro-6-iodo-7-(phenylsulfonyl)-7H-pyrrolo[2,3-d]pyrimidines from 4-chloro-7-(phenylsulfonyl)-7H-pyrrolo[2,3]pyrimidines: 4-chloro-7-(phenylsulfonyl)-7H-pyrrolo[2,3-d]pyrimidines (10.0 g, 34.0 mmol) was dissolved in anhydrous THF, protected by nitrogen gas (300 ml) and cooled to -78°C. Lithium diisopropylammonium (2M solution of THF/n-heptane/ethylbenzene, 26 mL, 51.1 mmol) was added slowly dropwise over 30 min using a syringe pump. After 1 hour of reaction, iodine (11.2 g, 44.3 mmol) dissolved in anhydrous THF (60 mL) was added dropwise over 30 minutes using a syringe pump. The reaction mixture was continued to be stirred for 1 hr, followed by the addition of 1 M HCl solution (180 ml). The reaction mixture was stirred until the temperature of the reaction mixture increased to 22°C and then concentrated. Dichloromethane (250 ml) and water (200 ml) were added to the concentrate and the organic layer was separated. The aqueous phase was extracted with dichloromethane (2 x 90 ml) and the combined organic phases were washed with brine (100 ml), dried over anhydrous sodium sulfate, filtered and concentrated. The crude product was recrystallized by acetonitrile (150 ml) to afford the light yellow solid product 4-chloro-6-iodo-7-(phenylsulfonyl)-7H-pyrrolo[2,3]pyrimidine (10.5 g, 25.1 mmol, 74% yield) with a melting point of 190 °C (decomposition). The purity of the product was 99% as determined by HPLC (retention time t R = 25.9 min).1H NMR (400 MHz, DMSO-d6) δ: 8.77 (s, 1H), 8.12-8.09 (m, 2H), 7.82-7.78 (m, 1H), 7.71-7.67 (m, 2H), 7.34 (s, 1H); 13C NMR (100 MHz, DMSO-d6) δ: 153.3, 152.1, 150.0, 137.2, 135.5, 130.0 (2C), 127.6 (2C), 120.6, 116.6, 84.6; IR (neat, cm-1): 1394, 1087, 724; HRMS (EI, m/z): 418.8988 (calculated value: C12H7ClIN3S, 418.8987, [M]+).

References

[1] ChemMedChem, 2014, vol. 9, # 11, p. 2516 - 2527
[2] Patent: WO2015/959, 2015, A1. Location in patent: Page/Page column 62-63
[3] Patent: WO2018/88780, 2018, A1. Location in patent: Page/Page column 13
[4] Patent: WO2015/89327, 2015, A1. Location in patent: Paragraph 0264
[5] Patent: WO2006/17443, 2006, A2. Location in patent: Page/Page column 56