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

Base Information

• Chemical Name: 5H-pyrrolo[3,2-d]pyrimidin-4-amine
• CAS No.: 2227-98-7
• Molecular Formula: C6H6N4
• Molecular Weight: 134.14
• Hs Code.: 2933990090
• NSC Number: 89405
• DSSTox Substance ID: DTXSID50415327
• Nikkaji Number: J1.424.839K
• Wikidata: Q27094438
• Metabolomics Workbench ID: 148020
• Mol file: 2227-98-7.mol

Synonyms:4-aminopyrrolopyrimidine

Chemical Property of 5H-pyrrolo[3,2-d]pyrimidin-4-amine

Chemical Property:

• Melting Point: 235-237 °C
• Boiling Point: 399.8 °C at 760 mmHg
• PKA: 13.84±0.40(Predicted)
• Flash Point: 224.4 °C
• PSA: 67.59000
• Density: 1.48 g/cm³
• LogP: 1.12130
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• XLogP3: 0.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 134.059246208
• Heavy Atom Count: 10
• Complexity: 127

Purity/Quality:

98%,99%, ^*data from raw suppliers

5H-pyrrolo[3,2-d]pyrimidin-4-amine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CNC2=C1N=CN=C2N

Technology Process of 5H-pyrrolo[3,2-d]pyrimidin-4-amine

There total 8 articles about 5H-pyrrolo[3,2-d]pyrimidin-4-amine 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: 80.0%

4-Chloro-5H-pyrrolo[3,2-d]pyrimidine (84905-80-6) → 9-Deazaadenine (2227-98-7)

Guidance literature:

With ammonium hydroxide; In 1,4-dioxane; at 160 ℃; for 20h;

DOI:10.1016/j.bmc.2008.05.056

Reference yield: 65.0%

ethyl 4-amino-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylate (2320-75-4) → 9-Deazaadenine (2227-98-7)

Guidance literature:

With water; potassium hydroxide; for 24h; Reflux;

DOI:10.1016/j.bmc.2015.07.059

Reference yield:

1,4-anhydro-2-deoxy-3,5-O-(di-tert-butylsilylene)-1-(4-N-pivaloylamino-pyrrolo[3,2-d]pyrimidin-7-yl)-4-thio-D-erythro-pento-1-enitol (1335287-29-0) → C24H39BN4O3SSi + 9-Deazaadenine (2227-98-7)

Guidance literature:

1,4-anhydro-2-deoxy-3,5-O-(di-tert-butylsilylene)-1-(4-N-pivaloylamino-pyrrolo[3,2-d]pyrimidin-7-yl)-4-thio-D-erythro-pento-1-enitol; With borane-THF; In tetrahydrofuran; at 0 ℃; for 18h; Inert atmosphere;

In tetrahydrofuran; methanol; at 0 ℃; for 1h; Inert atmosphere;

DOI:10.1021/jo201100n

upstream raw materials:

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

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

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

1,4-anhydro-2-deoxy-3,5-O-(di-tert-butylsilylene)-1-(4-N-pivaloylamino-pyrrolo[3,2-d]pyrimidin-7-yl)-4-thio-D-erythro-pento-1-enitol

Downstream raw materials:

(3R,4S)-1-((4-amino-5H-pyrrolo[3,2-d]pyrimidin-7-yl)methyl)-4-((methylthio)methyl)pyrrolidin-3-ol

(3S,4R)-1-[(9-deazaadenin-9-yl)methyl]-3-hydroxy-4-(methylthiomethyl)-pyrrolidine

Refernces

• 1、 Evans, Gary B.,Cameron, Scott A.,Luxenburger, Andreas,Guan, Rong,Suarez, Javier,Thomas, Keisha,Schramm, Vern L.,Tyler, Peter C.. "Tight binding enantiomers of pre-clinical drug candidates". . p. 5326 - 5333. Retrieved 2015/11/11.
• 2、 Haraguchi, Kazuhiro,Horii, Chikafumi,Yoshimura, Yuichi,Ariga, Fumiko,Tadokoro, Aya,Tanaka, Hiromichi. "An access to the β-anomer of 4′-thio-C-ribonucleosides: Hydroboration of 1-C-aryl- or 1-C-heteroaryl-4-thiofuranoid glycals and its regiochemical outcome". experimental part. p. 8658 - 8669. Retrieved 2012/01/05.