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

Melting point:

188-194 °C

Boiling point:

289.2±50.0 °C(Predicted)

Density 

1.61±0.1 g/cm3(Predicted)

vapor pressure 

0Pa at 25℃

storage temp. 

Keep in dark place,Inert atmosphere,2-8°C

solubility 

Soluble in DMSO, ethyl acetate and methanol.

pka

11.42±0.20(Predicted)

form 

Crystalline Powder

color 

White to tan

InChI

InChI=1S/C6H4ClN3/c7-5-4-1-2-8-6(4)10-3-9-5/h1-3H,(H,8,9,10)

InChIKey

BPTCCCTWWAUJRK-UHFFFAOYSA-N

SMILES

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

LogP

0.858 at 30℃

CAS DataBase Reference

3680-69-1(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,T,Xn

Risk Statements 

36/37/38-25-20/21/22

Safety Statements 

26-37-45-36

RIDADR 

UN 2811 6.1/PG 3

WGK Germany 

3

RTECS 

UY9360000

TSCA 

No

HazardClass 

IRRITANT

PackingGroup 

Ⅲ

HS Code 

29335990

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

Uses

4-Chloro-7H-pyrrolo[2,3-d] pyrimidine is an important pharmaceutical intermediate, which is widely used in the synthesis of many pharmaceutical intermediates at home and abroad. Including CP690550, CGP76030 and so on, 4-Chloro-7H-pyrrolo[2,3-d] pyrimidine was the scaffold for many commercially available drugs. Also, 4-Chloro-7H-pyrrolo[2,3-d] pyrimidine was the intermediate of the bulk drug, Tofatinib, which was widely used in treatment of adult patients with moderate to severe rheumatoid arthritis with inadequate or intolerant methotrexate response.

Chemical Properties

Lightbrown to brown crystalline powder

Uses

4-Chloro-7H-pyrrolo[2,3-d]pyrimidine is used in the manufacture of Tofacitinib citrate.

Synthesis

The preparation process of pyrimidine includes the first α -alkylation reaction between diethyl malonate and allyl bromide, and the subsequent cyclization reaction with amidine to obtain a six-membered ring of bislactam. The chlorination of carbonyl with phosphorus oxychloride to obtain dichloro pyrimidine ring, followed by the oxidation of the terminal double bond with potassium osmate hydrate and sodium periodate to obtain the aldehyde group. The final reaction with ammonia water to produce SNAr/cyclization reaction, a five-step reaction, total yield of 45.8% to obtain 4-Chloro-7H-pyrrolo[2,3-d]pyrimidine.

4-Chloro-7H-pyrrolo[2,3-d]pyrimidine(3680-69-1)Related Product Information

• Indole
• Pyrimidine
• Polyvinylpyrrolidone
• Epichlorohydrin
• 1-CHLOROMETHYL-1H-1,2,4-TRIAZOLE
• N-Methyl-2-pyrrolidone
• Sodium thiosulfate pentahydrate
• 4-Chloropyrimidine
• 6-Chloropurine
• DEAZAPURINE
• N-((3R,4R)-1-benzyl-4-Methylpiperidin-3-yl)-N-Methyl-7H-pyrrolo[2,3-d]pyriMidin-4-aMine
• (3R,4R)-1-Benzyl-N,4-dimethylpiperidin-3-amine
• Methyl 4-chloropicolinate
• 4-Chloropyridinium chloride
• 2-Pyridinecarbonitrile,4-hydroxy-(9CI)
• Lithium hydroxide monohydrate
• N-Methyl-N-((3S,4S)-4-Methylpiperidin-3-yl)-7H-pyrrolo[2,3-d]pyriMidin-4-aMine
• 1-BENZYL-N,4-DIMETHYLPIPERIDIN-3-AMINE DIHYDROCHLORIDE