(1S, 4R)-(4-(2,5-diamino-6-chloro-4-pyrimidinyl)amino)-2-cyclopenten-1-methanol

Base Information

• Chemical Name: (1S, 4R)-(4-(2,5-diamino-6-chloro-4-pyrimidinyl)amino)-2-cyclopenten-1-methanol
• CAS No.: 141271-12-7
• Molecular Formula: C₁₀H₁₄ClN₅O
• Molecular Weight: 255.707
• UNII: 5JVZ52Q6N8
• DSSTox Substance ID: DTXSID501135192
• Mol file: 141271-12-7.mol

Synonyms:(1S, 4R)-(4-(2,5-diamino-6-chloro-4-pyrimidinyl)amino)-2-cyclopenten-1-methanol

Chemical Property of (1S, 4R)-(4-(2,5-diamino-6-chloro-4-pyrimidinyl)amino)-2-cyclopenten-1-methanol

Chemical Property:

• Boiling Point: 561.0±60.0 °C(Predicted)
• Density: 1.517±0.06 g/cm3(Predicted)
• XLogP3: 0.6
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 3
• Exact Mass: 255.0886878
• Heavy Atom Count: 17
• Complexity: 290

Purity/Quality:

99%, ^*data from raw suppliers

4-(2,5-Diamino-6-chloropyrimidin-4-ylamino)cyclopent-2-enyl]methanol) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(C=CC1NC2=C(C(=NC(=N2)N)Cl)N)CO
• Isomeric SMILES: C1[C@@H](C=C[C@@H]1NC2=C(C(=NC(=N2)N)Cl)N)CO
• Uses: 4-(2,5-Diamino-6-chloropyrimidin-4-ylamino)cyclopent-2-enyl]methanol) is an impurity in the preparation of Abacavir (A105000), a nucleoside reverse transcriptase inhibitor (NRTI) (1,2,3).

Technology Process of (1S, 4R)-(4-(2,5-diamino-6-chloro-4-pyrimidinyl)amino)-2-cyclopenten-1-methanol

There total 14 articles about (1S, 4R)-(4-(2,5-diamino-6-chloro-4-pyrimidinyl)amino)-2-cyclopenten-1-methanol 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: 76.0%

(1S,4R)-4-(<2'-amino-6'-chloro-5'-<(4''-chlorophenyl)azo>pyrimidin-4'-yl>amino)cyclopent-2-enylmethanol (141271-13-8) → (1S, 4R)-(4-(2,5-diamino-6-chloro-4-pyrimidinyl)amino)-2-cyclopenten-1-methanol (141271-12-7,896716-96-4)

Guidance literature:

With zinc; In methanol; water; acetic acid; at 20 - 40 ℃; for 2h;

Reference yield: 53.0%

2,5-diamino-4,6-dichloropyrimidine (55583-59-0) + (1S,4R)-4-amino-2-cyclopentene-1-methanol tartrate salt → (1S, 4R)-(4-(2,5-diamino-6-chloro-4-pyrimidinyl)amino)-2-cyclopenten-1-methanol (141271-12-7,896716-96-4)

Guidance literature:

With sodium hydrogencarbonate; In butan-1-ol; at 95 ℃; for 16h;

Reference yield: 16.0%

Cyclopropylamine (765-30-0) + (1R,4S)-1-[(2-amino-6-chloro-5-formamido-4-pyrimidinyl)amino]-4-(hydroxymethyl)-2-cyclopentene (171887-04-0) → (1S, 4R)-(4-(2,5-diamino-6-chloro-4-pyrimidinyl)amino)-2-cyclopenten-1-methanol (141271-12-7,896716-96-4) + abacavir (136470-78-5,128131-83-9,136470-79-6)

Guidance literature:

In butan-1-ol; at 130 ℃; for 21h;

DOI:10.1080/15257770008033011

upstream raw materials:

(1S,4R)-4-(<2'-amino-6'-chloro-5'-<(4''-chlorophenyl)azo>pyrimidin-4'-yl>amino)cyclopent-2-enylmethanol

Cyclopropylamine

(1R,4S)-1-[(2-amino-6-chloro-5-formamido-4-pyrimidinyl)amino]-4-(hydroxymethyl)-2-cyclopentene

(-)-2-azabicyclo[2.2.1]hept-5-en-3-one

Downstream raw materials:

(1S,4R)-4-[2-amino-6-chloro-9H-purin-9-yl]-2-cyclopentene-1-methanol