1,2-Cyclopentanediol, 3-(5-amino-7-chloro-3H-1,2,3-triazolo(4,5-d)pyrimidin-3-yl)-5-(hydroxymethyl)-, rel-(1S,2S,3R,5R)-

Base Information

• Chemical Name: 1,2-Cyclopentanediol, 3-(5-amino-7-chloro-3H-1,2,3-triazolo(4,5-d)pyrimidin-3-yl)-5-(hydroxymethyl)-, rel-(1S,2S,3R,5R)-
• CAS No.: 108742-11-6
• Molecular Formula: C₁₀H₁₃ClN₆O₃
• Molecular Weight: 300.705
• DSSTox Substance ID: DTXSID70910864
• Wikidata: Q82880884
• Mol file: 108742-11-6.mol

Synonyms:108742-11-6;1,2-Cyclopentanediol, 3-(5-amino-7-chloro-3H-1,2,3-triazolo(4,5-d)pyrimidin-3-yl)-5-(hydroxymethyl)-, rel-(1S,2S,3R,5R)-;1,2-Cyclopentanediol, 3-(5-amino-7-chloro-3H-1,2,3-triazolo[4,5-d]pyrimidin-3-yl)-5-(hydroxymethyl)-, rel-(1S,2S,3R,5R)-;DTXSID70910864;(1S,2S,3R,5R)-3-(5-amino-7-chloro-triazolo[4,5-d]pyrimidin-3-yl)-5-(hydroxymethyl)cyclopentane-1,2-diol;3-(7-Chloro-5-imino-5,6-dihydro-3H-[1,2,3]triazolo[4,5-d]pyrimidin-3-yl)-5-(hydroxymethyl)cyclopentane-1,2-diol

Chemical Property of 1,2-Cyclopentanediol, 3-(5-amino-7-chloro-3H-1,2,3-triazolo(4,5-d)pyrimidin-3-yl)-5-(hydroxymethyl)-, rel-(1S,2S,3R,5R)-

Chemical Property:

• Vapor Pressure: 9.05E-19mmHg at 25°C
• Boiling Point: 668.3°Cat760mmHg
• Flash Point: 358°C
• Density: 2.21g/cm³
• XLogP3: -0.7
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 2
• Exact Mass: 300.0737660
• Heavy Atom Count: 20
• Complexity: 366

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(C(C(C1N2C3=C(C(=NC(=N3)N)Cl)N=N2)O)O)CO
• Isomeric SMILES: C1[C@@H]([C@@H]([C@H]([C@@H]1N2C3=C(C(=NC(=N3)N)Cl)N=N2)O)O)CO

Technology Process of 1,2-Cyclopentanediol, 3-(5-amino-7-chloro-3H-1,2,3-triazolo(4,5-d)pyrimidin-3-yl)-5-(hydroxymethyl)-, rel-(1S,2S,3R,5R)-

There total 5 articles about 1,2-Cyclopentanediol, 3-(5-amino-7-chloro-3H-1,2,3-triazolo(4,5-d)pyrimidin-3-yl)-5-(hydroxymethyl)-, rel-(1S,2S,3R,5R)- 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: 70.0%

(+/-)-(1α,2β,3α,5α)-3-<(2,5-diamino-6-chloro-4-pyrimidyl)amino>-5-(hydroxymethyl)-1,2-cyclopentanediol (108742-07-0) → (+/-)-(1α,2β,3α,5α)-3-(5-amino-7-chloro-3H-1,2,3-triazolo<4,5-d>pyrimidin-3-yl)-5-(hydroxymethyl)-1,2-cyclopentanediol (108742-11-6)

Guidance literature:

With acetic acid; sodium nitrite; 1.) 0 deg C, 2 h, 2.) RT, 1 h;

DOI:10.1021/jm00394a017

Reference yield:

(+/-)-(1α,2β,3α,5α)-3-<(2-amino-6-chloro-4-pyrimidinyl)amino>-5-(hydroxymethyl)-1,2-cyclopentanediol (108742-05-8) → (+/-)-(1α,2β,3α,5α)-3-(5-amino-7-chloro-3H-1,2,3-triazolo<4,5-d>pyrimidin-3-yl)-5-(hydroxymethyl)-1,2-cyclopentanediol (108742-11-6)

Guidance literature:

Multi-step reaction with 3 steps

1: sodium acetate trihydrate, acetic acid / H₂O / Ambient temperature

2: 54 percent / zinc, acetic acid / H₂O; ethanol / 1.5 h / Heating

3: 70 percent / sodium nitrite, aq. acetic acid / 1.) 0 deg C, 2 h, 2.) RT, 1 h

With sodium acetate; acetic acid; zinc; sodium nitrite; In ethanol; water;

DOI:10.1021/jm00394a017

Reference yield:

(+/-)-(1α,2β,3α,5α)-3-<<2-amino-6-chloro-5-<(4-chlorophenyl)azo>-4-pyrimidyl>amino>-5-(hydroxymethyl)-1,2-cyclopentanediol (108742-06-9) → (+/-)-(1α,2β,3α,5α)-3-(5-amino-7-chloro-3H-1,2,3-triazolo<4,5-d>pyrimidin-3-yl)-5-(hydroxymethyl)-1,2-cyclopentanediol (108742-11-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 54 percent / zinc, acetic acid / H₂O; ethanol / 1.5 h / Heating

2: 70 percent / sodium nitrite, aq. acetic acid / 1.) 0 deg C, 2 h, 2.) RT, 1 h

With acetic acid; zinc; sodium nitrite; In ethanol; water;

DOI:10.1021/jm00394a017

upstream raw materials:

(+/-)-(1α,2β,3α,5α)-3-<(2,5-diamino-6-chloro-4-pyrimidyl)amino>-5-(hydroxymethyl)-1,2-cyclopentanediol

(+/-)-(1α,2β,3α,5α)-3-<(2-amino-6-chloro-4-pyrimidinyl)amino>-5-(hydroxymethyl)-1,2-cyclopentanediol

(+/-)-(1α,2β,3α,5α)-3-<<2-amino-6-chloro-5-<(4-chlorophenyl)azo>-4-pyrimidyl>amino>-5-(hydroxymethyl)-1,2-cyclopentanediol

(+/-)-(1α,2β,3α,5α)-3-amino-5-(hydroxymethyl)-1,2-cyclopentanediol

Downstream raw materials:

(1α,2α,3β,5β)-(+/-)-3-<5-amino-7-(methylthio)-3H-1,2,3-triazolo<4,5-d>pyrimidin-3-yl>-5-(hydroxymethyl)-1,2-cyclopentanediol

(1R,2S,3R,5R)-3-(5-Amino-7-methoxy-[1,2,3]triazolo[4,5-d]pyrimidin-3-yl)-5-hydroxymethyl-cyclopentane-1,2-diol

(1α,2α,3β,5β)-(+/-)-3-(5,7-diamino-3H-1,2,3-triazolo<4,5-d>pyrimidin-3-yl)-5-(hydroxymethyl)-1,2-cyclopentanediol

(+/-)-5-amino-3,6-dihydro-3-<(1α,2β,3α,5α)-2,3-dihydroxy-4-(hydroxymethyl)cyclopentyl>-7H-1,2,3-triazol<4,5-d>pyrimidin-7-one