2-chloro-5-iodo-7H-pyrrolo[2,3-d]pyrimidine

2-chloro-5-iodo-7H-pyrrolo[2,3-d]pyrimidine Property

Density 

2.284±0.06 g/cm3(Predicted)

storage temp. 

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

pka

9.68±0.50(Predicted)

Appearance

Off-white to light brown Solid

Safety

HS Code 

2933599590

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P321Specific treatment (see … on this label).

P330Rinse mouth.

P332+P313IF SKIN irritation occurs: Get medical advice/attention.

P362Take off contaminated clothing and wash before reuse.

P501Dispose of contents/container to..…

2-chloro-5-iodo-7H-pyrrolo[2,3-d]pyrimidine Chemical Properties,Usage,Production

Synthesis

The general procedure for the synthesis of 2-chloro-5-iodo-7H-pyrrolo[2,3-d]pyrimidine using 2-chloro-7H-pyrrolo[2,3-d]pyrimidine as starting material was as follows: to a solution of 2-chloro-7H-pyrrolo[2,3-d]pyrimidine (482.5 g, 3.14 mol) in acetonitrile (2,500 mL) was added slowly at 12 °C with N-iodosuccinimide (742 g, 3.30 mol). The reaction mixture was stirred at room temperature for 1 hour, then aqueous sodium metabisulfite (650 g, dissolved in 4500 mL of water) was added. After continued stirring for 1 h, the solid product was collected by filtration to afford 2-chloro-5-iodo-7H-pyrrolo[2,3-d]pyrimidine as an orange solid in 82% yield (716.2 g). The structure of the product was confirmed by 1H NMR (400 MHz, DMSO-d6): δ 7.83 (s, 1H), 8.63 (s, 1H), 12.73 (s, 1H).

References

[1] Patent: WO2014/53967, 2014, A1. Location in patent: Page/Page column 134
[2] Journal of Medicinal Chemistry, 2016, vol. 59, # 22, p. 10084 - 10099
[3] Patent: WO2010/7116, 2010, A2. Location in patent: Page/Page column 91-92
[4] Patent: WO2010/7114, 2010, A2. Location in patent: Page/Page column 126