(1S–4R)-4-(2-amino-6-chloro-9H-purin-9-yl)-2-cyclopentene-1-methanol hydrochloride CAS#: 172015-79-1

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(1S–4R)-4-(2-amino-6-chloro-9H-purin-9-yl)-2-cyclopentene-1-methanol hydrochloride

Basic information Safety Supplier Related

(1S–4R)-4-(2-amino-6-chloro-9H-purin-9-yl)-2-cyclopentene-1-methanol hydrochloride Basic information

Product Name:

(1S–4R)-4-(2-amino-6-chloro-9H-purin-9-yl)-2-cyclopentene-1-methanol hydrochloride

Synonyms:

(1S–4R)-4-(2-amino-6-chloro-9H-purin-9-yl)-2-cyclopentene-1-methanol hydrochloride
( Abacavir USP Related Compound C)
Abacavir Impurity 8( Abacavir USP Related Compound C)
SIM 2142 (1S,4R)-4-(2-amino-6-chloro-9H-purin-9-yl)-2-cyclopentene-1-methanolhydrochloride 172015-79-1 100gm
(1S,4R)-4-(2-Amino-6-chloro-9H-purin-9-yl)-2-cyclopentene-1-methanol HCl
Abacavir Related Compound C (20 mg) ([(1S,4R)-4-(2-amino-6-chloro-9H-purin-9-yl)cyclopent-2-enyl]methanol hydrochloride)
(1S-cis)-4-(2-AMino-6-chloro-9H-purin-9-yl)-2-cyclopentene-1-Methanol Monohydrochloride
(1S,4R)-4-(2-AMino-6-chloro-9H-purin-yl)-2-cyclopentene-1-Methanol,HCl

CAS:

172015-79-1

MF:

C11H12ClN5O.ClH

MW:

302.164

Product Categories:

Nucleotides
Pharmaceuticals
Bases & Related Reagents
Intermediate
Intermediates & Fine Chemicals

Mol File:

172015-79-1.mol

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(1S–4R)-4-(2-amino-6-chloro-9H-purin-9-yl)-2-cyclopentene-1-methanol hydrochloride Chemical Properties

Melting point:: 165-170?C
storage temp.: Inert atmosphere,2-8°C
solubility: DMSO (Slightly), Methanol (Slightly)
color: Off-White to Beige to Brown

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Safety Information

HS Code: 2933599550

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(1S–4R)-4-(2-amino-6-chloro-9H-purin-9-yl)-2-cyclopentene-1-methanol hydrochloride Usage And Synthesis

Chemical Properties

Off-White to Tan Solid

Uses

Abacavir intermediate.

Synthesis

171887-04-0

172015-79-1

The general procedure for the synthesis of ((1S,4R)-4-(2-amino-6-chloro-9H-purin-9-yl)cyclopent-2-en-1-yl)methanol hydrochloride from abacavir intermediate A4 was as follows: to the reactor was added N-[2-amino-4-chloro-6-[[(1R,4S)-4-(hydroxymethyl)-2-cyclopenten-1-yl]amino]-5-pyrimidinyl] Formamide (0.1762 mol) and trichloromethylsilicate (7 vol). The reaction mixture was cooled to 0-5 °C and hydrochloric acid (0.7 vol) was added slowly at 0-10 °C. After addition, the reaction was held at 0-5 °C for 60 min. Subsequently, the reaction mixture was brought to room temperature and stirring was continued for 16-18 hours. Upon completion of the reaction, the solid product was collected by filtration and purified by recrystallization in methanol. (Yield: 76%, HPLC purity: 98.69%).

References

[1] Nucleosides, Nucleotides and Nucleic Acids, 2000, vol. 19, # 1-2, p. 297 - 327
[2] Patent: US2017/233329, 2017, A1. Location in patent: Paragraph 0054; 0055
[3] Patent: CN107641122, 2018, A. Location in patent: Paragraph 0016; 0049; 0055-0056; 0059-0073; 0076

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