5-benzyl-2,4-dichloro-5H-pyrrolo[3,2-d]pyrimidine

Base Information

• Chemical Name: 5-benzyl-2,4-dichloro-5H-pyrrolo[3,2-d]pyrimidine
• CAS No.: 129872-83-9
• Molecular Formula: C13H9Cl2N3
• Molecular Weight: 278.141
• Hs Code.: 2933990090
• ChEMBL ID: CHEMBL533291
• DSSTox Substance ID: DTXSID30563390
• Wikidata: Q82447821
• Mol file: 129872-83-9.mol

Synonyms:5-benzyl-2,4-dichloro-5H-pyrrolo[3,2-d]pyrimidine;129872-83-9;5-benzyl-2,4-dichloropyrrolo[3,2-d]pyrimidine;TCMDC-137801;CHEMBL533291;SCHEMBL1716185;DTXSID30563390;NFNHWZVKVVHLFG-UHFFFAOYSA-N;NSC807633;AKOS016845084;NSC-807633;EN300-6789196;J-516754;Z2044823719

Chemical Property of 5-benzyl-2,4-dichloro-5H-pyrrolo[3,2-d]pyrimidine

Chemical Property:

• PSA: 30.71000
• LogP: 3.78640
• Storage Temp.: 2-8°C
• XLogP3: 3.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 277.0173527
• Heavy Atom Count: 18
• Complexity: 283

Purity/Quality:

≥99% ^*data from raw suppliers

5-Benzyl-2,4-dichloro-5H-pyrrolo[3,2-d]pyrimidine 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)CN2C=CC3=C2C(=NC(=N3)Cl)Cl

Technology Process of 5-benzyl-2,4-dichloro-5H-pyrrolo[3,2-d]pyrimidine

There total 15 articles about 5-benzyl-2,4-dichloro-5H-pyrrolo[3,2-d]pyrimidine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 77.0%

5-benzyl-4-chloro-5H-pyrrolo[3,2-d]pyrimidin-2-amine (914496-94-9) → 5-benzyl-2,4-dichloro-5H-pyrrolo<3,2-d>pyrimidine (129872-83-9)

Guidance literature:

5-benzyl-4-chloro-5H-pyrrolo[3,2-d]pyrimidin-2-amine; With antimony(III) chloride; In 1,2-dichloro-ethane; at -10 ℃; for 0.0833333h;

With tert.-butylnitrite; In 1,2-dichloro-ethane; at -10 - 20 ℃; for 5h;

Reference yield: 50.0%

benzyl bromide (100-39-0) + 2,4-dichloro-5H-pyrrolo[3,2-d]pyrimidine (63200-54-4) → 5-benzyl-2,4-dichloro-5H-pyrrolo<3,2-d>pyrimidine (129872-83-9)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20 ℃; for 16h; Sealed tube;

DOI:10.1021/acs.jmedchem.7b00365

Reference yield:

(E)-N'-(3-benzyl-4-oxo-4,5-dihydro-3H-pyrrolo[3,2-d]pyrimidin-2-yl)-N,N-dimethylformimidamide → 5-benzyl-2,4-dichloro-5H-pyrrolo<3,2-d>pyrimidine (129872-83-9)

Guidance literature:

Multi-step reaction with 5 steps

1.1: sodium hydroxide; water / methanol / 5 h / 100 °C

2.1: ammonium formate / palladium 10% on activated carbon / methanol / 4 h / 75 °C

3.1: sodium hydroxide; tetrabutylammomium bromide / dichloromethane; water / 2 h / 0 - 20 °C

4.1: trichlorophosphate / 3 h / 116 °C

5.1: antimony(III) chloride / 1,2-dichloro-ethane / 0.08 h / -10 °C

5.2: 5 h / -10 - 20 °C

With sodium hydroxide; tetrabutylammomium bromide; water; ammonium formate; antimony(III) chloride; trichlorophosphate; palladium 10% on activated carbon; In methanol; dichloromethane; water; 1,2-dichloro-ethane;

upstream raw materials:

benzyl bromide

2,4-dichloro-5H-pyrrolo[3,2-d]pyrimidine

5-benzyl-4-chloro-5H-pyrrolo[3,2-d]pyrimidin-2-amine

(E)-N,N-dimethyl-N'-(4-methyl-5-nitro-6-oxo-1,6-dihydropyrimidin-2-yl)formimidamide

Downstream raw materials:

5-benzyl-2-chloro-5H-pyrrolo<3,2-d>pyrimidin-4(3H)-one

1-(4-(5-benzyl-2-chloro-5H-pyrrolo[3,2-d]pyrimidin-4-yloxy)-3,5-dimethylphenyl)ethanone

5-benzyl-2-chloro-4-(2,6-dimethyl-4-nitrophenoxy)-5H-pyrrolo[3,2-d]pyrimidine

2,4-dichloro-5H-pyrrolo[3,2-d]pyrimidine

Refernces

• 1、 McGowan, David C.,Herschke, Florence,Pauwels, Frederik,Stoops, Bart,Smyej, Ilham,Last, Stefaan,Pieters, Serge,Embrechts, Werner,Khamlichi, Mourad Daoubi,Thoné, Tine,Van Schoubroeck, Bertrand,Mostmans, Wendy,Wuyts, Debbie,Verstappen, Dorien,Scholliers, Annick,De Pooter, Dorien,Dhuyvetter, Deborah,Borghys, Herman,Tuefferd, Marianne,Arnoult, Eric,Hong, Jin,Fanning, Gregory,Bollekens, Jacques,Urmaliya, Vijay,Teisman, Ard,Horton, Helen,Jonckers, Tim H. M.,Raboisson, Pierre. "Identification and Optimization of Pyrrolo[3,2-d]pyrimidine Toll-like Receptor 7 (TLR7) Selective Agonists for the Treatment of Hepatitis B". . p. 6137 - 6151. Retrieved 2017/08/02.
• 2、 -. "DIARYL-PURINE, AZAPURINES AND -DEAZAPURINES AS NON-NUCLEOSIDE REVERSE TRANSCRIPTASE INHIBITORS FOR TREATMENT OF HIV". Page/Page column 33; 43. . Retrieved 2008/06/13.