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

Base Information

• Chemical Name: (+/-)-(1α,2α,3α,5α)-3-<(2-amino-6-chloro-4-pyrimidinyl)amino>-5-(hydroxymethyl)-1,2-cyclopentanediol
• CAS No.: 125073-22-5
• Molecular Formula: C₁₀H₁₅ClN₄O₃
• Molecular Weight: 274.707
• Mol file: 125073-22-5.mol

Synonyms:

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 2 articles about (+/-)-(1α,2α,3α,5α)-3-<(2-amino-6-chloro-4-pyrimidinyl)amino>-5-(hydroxymethyl)-1,2-cyclopentanediol 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: 72.0%

2-Amino-4,6-dichloropyrimidine (56-05-3) + (1R,2S,3R,4R)-2,3-dihydroxy-4-(hydroxylmethyl)-1-aminocyclopentan hydrochloride (79200-57-0) → 3-(2-amino-6-chloro-pyrimidin-4-ylamino)-5-hydroxymethyl-cyclopentane-1,2-diol (50619-38-0,75829-34-4,108742-05-8,125073-22-5)

Guidance literature:

With triethylamine; In ethanol; for 16h; Reflux;

DOI:10.1016/j.bmcl.2011.11.091

Reference yield:

→ 3-(2-amino-6-chloro-pyrimidin-4-ylamino)-5-hydroxymethyl-cyclopentane-1,2-diol (50619-38-0,75829-34-4,108742-05-8,125073-22-5)

Guidance literature:

2-Amino-4,6-dichlorpyrimidin (I), trans-3-Amino-trans-5-(hydroxymethyl)-cis-1,2-cyclopentandiol / Ethanol, Triethylamin;

DOI:10.1002/jps.2600620907

Reference yield:

(+/-)-(1α,2α,3α,5α)-3-<(2-amino-6-chloro-4-pyrimidinyl)amino>-5-(hydroxymethyl)-1,2-cyclopentanediol (125073-22-5) → (+/-)-(1α,2α,3α,5α)-3-(2,6-diamino-9H-purin-9-yl)-5-(hydroxymethyl)-1,2-cyclopentanediol (125073-27-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) conc. HCl, NaNO₂, 2.) sodium acetate, glacial acetic acid / 1.) H₂O, 0 deg C, 0.5 h, 2.) RT, 42 h

2: 68.4 percent / Zn-glacial acetic acid / H₂O; ethanol / 2.5 h / Heating

3: 1.) conc. HCl, 2.) 0.5 N HCl / 1.) DMF, RT, 2.) 2.5 h

4: 51.7 percent / liquid NH₃ / methanol / 57 h / 75 °C

With hydrogenchloride; ammonia; sodium acetate; acetic acid; zinc; sodium nitrite; In methanol; ethanol; water;

DOI:10.1021/jm00166a020

upstream raw materials:

2-Amino-4,6-dichloropyrimidine

(1R,2S,3R,4R)-2,3-dihydroxy-4-(hydroxylmethyl)-1-aminocyclopentan hydrochloride

Downstream raw materials:

(+/-)-(1α,2α,3α,5α)-3-(2-amino-6-chloro-9H-purin-9-yl)-5-(hydroxymethyl)-1,2-cyclopentanediol

(+/-)-(1α,2α,3α,5α)-3-(2,6-diamino-9H-purin-9-yl)-5-(hydroxymethyl)-1,2-cyclopentanediol

(+/-)-(1α,2α,3α,5α)-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,2α,3α,4α)-2,3-dihydroxy-4-(hydroxymethyl)cyclopentyl>-7H-1,2,3-triazolo<4,5-d>pyrimidin-7-one

Refernces

• 1、 Shealy,Clayton. "Carbocyclic analogs of guanosine and 8 azaguanosine". . p. 1432 - 1434. Retrieved 2007/10/09.