5-bromo-7-(beta-D-ribofuranosyl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine

Base Information

• Chemical Name: 5-bromo-7-(beta-D-ribofuranosyl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine
• CAS No.: 21193-80-6
• Molecular Formula: C11H13BrN4O4
• Molecular Weight: 345.153
• NSC Number: 103802
• DSSTox Substance ID: DTXSID60943525
• Mol file: 21193-80-6.mol

Synonyms:5-Bromotubercidin;NSC103802;DTXSID60943525;ZWTPRQXZXQEKFT-UHFFFAOYSA-N;ZINC01680588;NSC-103802;5-bromo-7-(beta-D-ribofuranosyl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine

Chemical Property of 5-bromo-7-(beta-D-ribofuranosyl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine

Chemical Property:

• Vapor Pressure: 8.16E-20mmHg at 25°C
• Melting Point: 232 °C(Solv: methanol (67-56-1))
• Boiling Point: 686.9°C at 760 mmHg
• PKA: 12.32±0.70(Predicted)
• Flash Point: 369.2°C
• PSA: 126.65000
• Density: 2.26g/cm³
• LogP: -0.03130
• XLogP3: -0.7
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 2
• Exact Mass: 344.01202
• Heavy Atom Count: 20
• Complexity: 365

Purity/Quality:

97% ^*data from raw suppliers

5-?Bromotubercidin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=C(C2=C(N=CN=C2N1C3C(C(C(O3)CO)O)O)N)Br

Technology Process of 5-bromo-7-(beta-D-ribofuranosyl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine

There total 5 articles about 5-bromo-7-(beta-D-ribofuranosyl)-7H-pyrrolo[2,3-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%

7-bromo-2',3',5'-tri-O-acetyltubercidin → 5-Bromotubercidin (21193-80-6,21193-61-3)

Guidance literature:

With ammonia; In methanol; at 20 ℃; for 8h; Inert atmosphere;

DOI:10.1016/j.tetlet.2016.08.053

Reference yield: 78.0%

(2R,3R,4R,5R)-2-((benzoyloxy)methyl)-5-(5-bromo-4-chloro-7H-pyrrolo[2,3-d]pyrimidin-7-yl)tetrahydrofuran-3,4-diyl dibenzoate (952429-11-7) → 5-Bromotubercidin (21193-80-6,21193-61-3)

Guidance literature:

With ammonia; In methanol; at 120 - 130 ℃; for 16h; Sealed tube;

Reference yield:

C9H11BrClN3Si → 5-Bromotubercidin (21193-80-6,21193-61-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 723 mg / trimethylsilyl trifluoromethanesulfonate / acetonitrile / 1 h / 80 °C

2: 61 percent / ammonia / methanol / 120 - 130 °C

With trimethylsilyl trifluoromethanesulfonate; ammonia; In methanol; acetonitrile; 1: silyl-Hilbert-Johnson reaction;

DOI:10.1016/j.tet.2007.06.107

upstream raw materials:

(2R,3R,4R,5R)-2-((benzoyloxy)methyl)-5-(5-bromo-4-chloro-7H-pyrrolo[2,3-d]pyrimidin-7-yl)tetrahydrofuran-3,4-diyl dibenzoate

5-bromo-4-chloro-7H-pyrrolo[2,3-d]pyrimidine

2',3',5'-tri-O-acetyltubercidin

Downstream raw materials:

(2R,3R,4R,5R)-2-(4-amino-5-bromo-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-5-(chloromethyl)tetra-hydrofuran-3,4-diol

4-amino-N7-(3'-deoxy-β-D-ribofuranosyl)pyrrolo[2,3-d]pyrimidine

4-amino-5-(4-methoxyphenyl)-7-(β-D-ribofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine

4-amino-5-phenyl-7-(β-D-ribofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine