172015-79-1

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 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;[(1R,4S)-4-(2-Amino-6-chloro-9H-purin-9-yl)cyclopent-2-en-1-yl]methanol;Abacavir Related CoMpound C;((1S,4R)-4-(2-Amino-6-chloro-9H-purin-9-yl)cyclopent-2-en-1-yl)methanol hydrochloride;(1S,4R)-4-(2-amino-6-chloro-9H-purin-9-yl) -2-Cyclopentene-1- methano Hydrochloride
• CAS NO: 172015-79-1
• Molecular Formula: C₁₁H₁₂ClN₅O*ClH
• Molecular Weight: 302.164
• EINECS: 426-200-1
• Product Categories: Bases & Related Reagents;Intermediate;Intermediates & Fine Chemicals;Nucleotides;Pharmaceuticals
• Mol File: 172015-79-1.mol
• Article Data: 5

Chemical Properties

• Melting Point: 165-170?C
• Boiling Point: 572°C at 760 mmHg
• Flash Point: 299.7°C
• Appearance: /
• Vapor Pressure: 6.37E-14mmHg at 25°C
• Storage Temp.: Refrigerator, Under Inert Atmosphere
• Solubility: DMSO (Slightly), Methanol (Slightly)
• CAS DataBase Reference: (1S–4R)-4-(2-amino-6-chloro-9H-purin-9-yl)-2-cyclopentene-1-methanol hydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: (1S–4R)-4-(2-amino-6-chloro-9H-purin-9-yl)-2-cyclopentene-1-methanol hydrochloride(172015-79-1)
• EPA Substance Registry System: (1S–4R)-4-(2-amino-6-chloro-9H-purin-9-yl)-2-cyclopentene-1-methanol hydrochloride(172015-79-1)

Safety Data

• Hazardous Substances Data: 172015-79-1(Hazardous Substances Data)

Usage

Chemical Properties

Off-White to Tan Solid

InChI:InChI=1/C11H12ClN5O.ClH/c12-9-8-10(16-11(13)15-9)17(5-14-8)7-2-1-6(3-7)4-18;/h1-2,5-7,18H,3-4H2,(H2,13,15,16);1H/t6-,7+;/m1./s1

Synthetic route

(1R,4S)-1-[(2-amino-6-chloro-5-formamido-4-pyrimidinyl)amino]-4-(hydroxymethyl)-2-cyclopentene (171887-04-0) → ((1S,4R)-4-(2-amino-6-chloro-9H-purin-9-yl)cyclopent-2-en-1-yl)methanol hydrochloride (172015-79-1)

Conditions	Yield
With hydrogenchloride; orthoformic acid triethyl ester In water for 4h; Cyclization;	92%
With hydrogenchloride; orthoformic acid triethyl ester In water at 0 - 10℃; for 1h; Concentration; Temperature;	76%
With hydrogenchloride; orthoformic acid triethyl ester In ethanol at 0 - 10℃; for 10h;	72.2%

orthoformic acid triethyl ester (122-51-0) + (1R,4S)-1-[(2-amino-6-chloro-5-formamido-4-pyrimidinyl)amino]-4-(hydroxymethyl)-2-cyclopentene (171887-04-0) → ((1S,4R)-4-(2-amino-6-chloro-9H-purin-9-yl)cyclopent-2-en-1-yl)methanol hydrochloride (172015-79-1)

Conditions	Yield
With hydrogenchloride In tetrahydrofuran; industrial methylated spirit; water at 0 - 25℃; Product distribution / selectivity;	82%
With hydrogenchloride In industrial methylated spirit; water at 0 - 25℃; Product distribution / selectivity;	81%

(-)-2-azabicyclo[2.2.1]hept-5-en-3-one (79200-56-9) → ((1S,4R)-4-(2-amino-6-chloro-9H-purin-9-yl)cyclopent-2-en-1-yl)methanol hydrochloride (172015-79-1)

Conditions	Yield
Multi-step reaction with 4 steps 1: 1.264 g / tetrahydrofuran; H2O / 18 h / 20 - 60 °C 2: 90.5 percent / LiAlH4 / tetrahydrofuran / 19.5 h / 0 °C / Heating 3: 83 percent / Et3N / ethanol / 7 h / Heating 4: 92 percent / triethylorthoformate; HCl / H2O / 4 h View Scheme

(1R,4S)-1-amino-4-hydroxymethyl-2-cyclopentene (136522-35-5) → ((1S,4R)-4-(2-amino-6-chloro-9H-purin-9-yl)cyclopent-2-en-1-yl)methanol hydrochloride (172015-79-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: 83 percent / Et3N / ethanol / 7 h / Heating 2: 92 percent / triethylorthoformate; HCl / H2O / 4 h View Scheme

N-(2-amino-4,6-dichloropyrimidin-5-yl)formamide (171887-03-9) → ((1S,4R)-4-(2-amino-6-chloro-9H-purin-9-yl)cyclopent-2-en-1-yl)methanol hydrochloride (172015-79-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: 83 percent / Et3N / ethanol / 7 h / Heating 2: 92 percent / triethylorthoformate; HCl / H2O / 4 h View Scheme
Multi-step reaction with 2 steps 1.1: sodium hydrogencarbonate / ethanol / 0.5 h / 20 °C / Inert atmosphere 1.2: 3 h / 75 - 80 °C / Inert atmosphere 2.1: orthoformic acid triethyl ester; hydrogenchloride / ethanol / 10 h / 0 - 10 °C View Scheme

2-amino-5-{[(dimethylamino)methylene]amino}-4,6-dichloropyrimidine (171887-02-8) → ((1S,4R)-4-(2-amino-6-chloro-9H-purin-9-yl)cyclopent-2-en-1-yl)methanol hydrochloride (172015-79-1)

Conditions	Yield
Multi-step reaction with 3 steps 1: 72 percent / aq. phosphate buffer / 4 h / pH 3.2 / Heating 2: 83 percent / Et3N / ethanol / 7 h / Heating 3: 92 percent / triethylorthoformate; HCl / H2O / 4 h View Scheme

(-)-(1S, 4R)-4-amino-2-cyclopentene-1-carboxylic acid methanesulfonate → ((1S,4R)-4-(2-amino-6-chloro-9H-purin-9-yl)cyclopent-2-en-1-yl)methanol hydrochloride (172015-79-1)

Conditions	Yield
Multi-step reaction with 3 steps 1: 90.5 percent / LiAlH4 / tetrahydrofuran / 19.5 h / 0 °C / Heating 2: 83 percent / Et3N / ethanol / 7 h / Heating 3: 92 percent / triethylorthoformate; HCl / H2O / 4 h View Scheme

(1S,4R)-4-amino-2-cyclopentene-1-methanol tartrate salt + 4,6-dichloro-2,5-diformamido-pyrimidine (116477-30-6) → ((1S,4R)-4-(2-amino-6-chloro-9H-purin-9-yl)cyclopent-2-en-1-yl)methanol hydrochloride (172015-79-1)

Conditions	Yield
Stage #1: (1S,4R)-4-amino-2-cyclopentene-1-methanol tartrate salt With sodium carbonate In ethanol for 0.5h; Stage #2: 4,6-dichloro-2,5-diformamido-pyrimidine In ethanol for 3h; Heating / reflux; Stage #3: With hydrogenchloride; orthoformic acid triethyl ester more than 3 stages;

Cyclopropylamine (765-30-0) + ((1S,4R)-4-(2-amino-6-chloro-9H-purin-9-yl)cyclopent-2-en-1-yl)methanol hydrochloride (172015-79-1) → abacavir (136470-78-5)

Conditions	Yield
In methanol at 70℃; for 12h; Substitution;	90%
Stage #1: (1S,cis)-4-(2-amino-6-chloro-9-H-purin-9-yl)-2-cyclopentene-1-methanol hydrochloride With triethylamine In water Stage #2: Cyclopropylamine In water at 70 - 75℃; Concentration; Solvent; Temperature;	90%
In isopropyl alcohol at 90 - 95℃; for 12h; sealed reactor;
In ethanol at 25 - 78℃; for 6h;
With sodium carbonate In ethanol at 70 - 80℃;	25 g

pyrographite (7440-44-0) + Cyclopropylamine (765-30-0) + ((1S,4R)-4-(2-amino-6-chloro-9H-purin-9-yl)cyclopent-2-en-1-yl)methanol hydrochloride (172015-79-1) → abacavir (136470-78-5)

Conditions	Yield
With sodium hydroxide In acetone	90%

(1R,4S)-1-amino-4-(hydroxymethyl)-2-cyclopentene hydrochloride + ((1S,4R)-4-(2-amino-6-chloro-9H-purin-9-yl)cyclopent-2-en-1-yl)methanol hydrochloride (172015-79-1) → ((1S,4R)-4-(2-amino-6-((1R,4S)-4-(hydroxymethyl)cyclopentyl-2-enylamino)-9H-purin-9-yl)cyclopent-2-enyl) methanol

Conditions	Yield
With sodium carbonate In ethanol at 75 - 80℃; for 6h; Solvent; Reagent/catalyst; Inert atmosphere;	87.1%

((1S,4R)-4-(2-amino-6-chloro-9H-purin-9-yl)cyclopent-2-en-1-yl)methanol hydrochloride (172015-79-1) → (1R,cis)-3-[2-amino-6-(cyclopropylamino)-9H-purin-9-yl]-1-cyclopentane-1-methanol

Conditions	Yield
Multi-step reaction with 2 steps 1: 90 percent / methanol / 12 h / 70 °C 2: 98 percent / H2 / Pd-C / ethanol / 1.5 h / 2585.74 Torr View Scheme

((1S,4R)-4-(2-amino-6-chloro-9H-purin-9-yl)cyclopent-2-en-1-yl)methanol hydrochloride (172015-79-1) → (1S,4R)-4-[2-amino-6-chloro-9H-purin-9-yl]-2-cyclopentene-1-methanol (136522-33-3)

Conditions	Yield
With ammonia In water at 10 - 15℃; for 1h; pH=7 - 7.5;

((1S,4R)-4-(2-amino-6-chloro-9H-purin-9-yl)cyclopent-2-en-1-yl)methanol hydrochloride (172015-79-1) → (1S,4R)-4-[2-amino-6-(cyclopropylamino)-9H-purin-9-yl]-2-cyclopentene-1-methanol hydrobromide (1280727-16-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: ethanol / 6 h / 25 - 78 °C 2: hydrogen bromide / ethanol; water / 0.75 h / 25 - 30 °C View Scheme

((1S,4R)-4-(2-amino-6-chloro-9H-purin-9-yl)cyclopent-2-en-1-yl)methanol hydrochloride (172015-79-1) → (1S,4R)-4-[2-amino-6-(cyclopropylamino)-9H-purin-9-yl]-2-cyclopentene-1-methanol malonate (1280629-49-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: ethanol / 6 h / 25 - 78 °C 2: ethanol / 0.75 h / 25 - 70 °C View Scheme

((1S,4R)-4-(2-amino-6-chloro-9H-purin-9-yl)cyclopent-2-en-1-yl)methanol hydrochloride (172015-79-1) → (1S,4R)-4-[2-amino-6-(cyclopropylamino)-9H-purin-9-yl]-2-cyclopentene-1-methanol maleate (1280629-56-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: ethanol / 6 h / 25 - 78 °C 2: ethanol / 0.25 h / 25 - 30 °C View Scheme

((1S,4R)-4-(2-amino-6-chloro-9H-purin-9-yl)cyclopent-2-en-1-yl)methanol hydrochloride (172015-79-1) → (1S,4R)-4-[2-amino-6-(cyclopropylamino)-9H-purin-9-yl]-2-cyclopentene-1-methanol monooxalate (1280629-52-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: ethanol / 6 h / 25 - 78 °C 2: ethanol; water / 2.25 h / 0 - 75 °C View Scheme

((1S,4R)-4-(2-amino-6-chloro-9H-purin-9-yl)cyclopent-2-en-1-yl)methanol hydrochloride (172015-79-1) → (1S,4R)-4-[2-amino-6-(cyclopropylamino)-9H-purin-9-yl]-2-cyclopentene-1-methanol dihydrobromide

Conditions	Yield
Multi-step reaction with 2 steps 1: ethanol / 6 h / 25 - 78 °C 2: hydrogen bromide / ethanol; water / 0.75 h / 25 - 30 °C View Scheme

Reaxys ID: 32100528 + ((1S,4R)-4-(2-amino-6-chloro-9H-purin-9-yl)cyclopent-2-en-1-yl)methanol hydrochloride (172015-79-1) → Reaxys ID: 32100526

di-tert-butyl diisopropylphosphoramide (137348-86-8) + 3-chloro-benzenecarboperoxoic acid (937-14-4) + ((1S,4R)-4-(2-amino-6-chloro-9H-purin-9-yl)cyclopent-2-en-1-yl)methanol hydrochloride (172015-79-1) → ((1S,4R)-4-(2-amino-6-chloro-9H-purin-9-yl)cyclopent-2-en-1-yl)methyl di-tert-butyl phosphate

Conditions	Yield
Stage #1: di-tert-butyl diisopropylphosphoramide; ((1S,4R)-4-(2-amino-6-chloro-9H-purin-9-yl)cyclopent-2-en-1-yl)methanol hydrochloride With 1H-tetrazole In dichloromethane at 20℃; for 1h; Stage #2: 3-chloro-benzenecarboperoxoic acid In dichloromethane at -40 - -10℃; for 2.33333h;	161 mg

2-methoxyethylamine (109-85-3) + ((1S,4R)-4-(2-amino-6-chloro-9H-purin-9-yl)cyclopent-2-en-1-yl)methanol hydrochloride (172015-79-1) → ((1S,4R)-4-(2-amino-6-((2-methoxyethyl)amino)-9H-purin-9-yl)cyclopent-2-en-1-yl)methanol

Conditions	Yield
In tetrahydrofuran; ethanol at 120℃; for 0.75h; Microwave irradiation;	81 mg

((1S,4R)-4-(2-amino-6-chloro-9H-purin-9-yl)cyclopent-2-en-1-yl)methanol hydrochloride (172015-79-1) → carbovir (120443-30-3)

Conditions	Yield
With sodium hydroxide In water at 130℃; for 1h; Microwave irradiation;	55 mg

((1S,4R)-4-(2-amino-6-chloro-9H-purin-9-yl)cyclopent-2-en-1-yl)methanol hydrochloride (172015-79-1) → 2-(((1S,4R)-4-(2-amino-6-methoxy-9H-purin-9-yl)cyclopent-2-en-1-yl)methoxy)-4H-benzo[d][1,3,2]dioxaphosphinine 2-oxide

Conditions	Yield
Multi-step reaction with 2 steps 1: methanol / 6 h / 20 °C 2: 1-methyl-1H-imidazole / acetonitrile / 0.5 h / 20 °C / Inert atmosphere View Scheme

((1S,4R)-4-(2-amino-6-chloro-9H-purin-9-yl)cyclopent-2-en-1-yl)methanol hydrochloride (172015-79-1) → ((1S,4R)-4-(2-amino-6-chloro-9H-purin-9-yl)cyclopent-2-en-1-yl)methyl dihydrogen phosphate hydrochloride

Conditions	Yield
Multi-step reaction with 2 steps 1.1: 1H-tetrazole / dichloromethane / 1 h / 20 °C 1.2: 2.33 h / -40 - -10 °C 2.1: hydrogenchloride / ethyl acetate / 3 h / 20 °C View Scheme

((1S,4R)-4-(2-amino-6-chloro-9H-purin-9-yl)cyclopent-2-en-1-yl)methanol hydrochloride (172015-79-1) → ((1S,4R)-4-(2-amino-6-methoxy-9H-purin-9-yl)cyclopent-2-en-1-yl)methyl dihydrogen phosphate

Conditions	Yield
Multi-step reaction with 3 steps 1.1: 1H-tetrazole / dichloromethane / 1 h / 20 °C 1.2: 2.33 h / -40 - -10 °C 2.1: hydrogenchloride / ethyl acetate / 3 h / 20 °C 3.1: methanol / 2.5 h / 50 - 60 °C / Microwave irradiation View Scheme

((1S,4R)-4-(2-amino-6-chloro-9H-purin-9-yl)cyclopent-2-en-1-yl)methanol hydrochloride (172015-79-1) → ((1S,4R)-4-(2-amino-6-mercapto-9H-purin-9-yl)cyclopent-2-en-1-yl)methanol

Conditions	Yield
With sodium hydrogensulfide In ethanol; water at 20℃; for 18h;	11 mg

methyl ((4-bromophenoxy)(4-nitrophenoxy)phosphoryl)-L-alaninate + ((1S,4R)-4-(2-amino-6-chloro-9H-purin-9-yl)cyclopent-2-en-1-yl)methanol hydrochloride (172015-79-1) → methyl ((((1S,4R)-4-(2-amino-6-chloro-9H-purin-9-yl)cyclopent-2-en-1-yl)methoxy)(4-bromophenoxy)phosphoryl)-L-alaninate

Conditions	Yield
With tert-butylmagnesium chloride In tetrahydrofuran at 20℃; Inert atmosphere;	7.16 mg

sodium methylate (124-41-4) + ((1S,4R)-4-(2-amino-6-chloro-9H-purin-9-yl)cyclopent-2-en-1-yl)methanol hydrochloride (172015-79-1) → ((1S,4R)-4-(2-amino-6-methoxy-9H-purin-9-yl)cyclopent-2-en-1-yl)methanol (190951-74-7)

Conditions	Yield
With methanol at 20℃; for 6h;	0.47 g

dimethyl amine (124-40-3) + ((1S,4R)-4-(2-amino-6-chloro-9H-purin-9-yl)cyclopent-2-en-1-yl)methanol hydrochloride (172015-79-1) → ((1S,4R)-4-(2-amino-6-(dimethylamino)-9H-purin-9-yl)cyclopent-2-en-1-yl)methanol

Conditions	Yield
In ethanol; water at 20℃; for 1h;	20 mg

methylamine (74-89-5) + ((1S,4R)-4-(2-amino-6-chloro-9H-purin-9-yl)cyclopent-2-en-1-yl)methanol hydrochloride (172015-79-1) → (+/-)-cis-4-(2-Amino-6-methylamino-9H-purin-9-yl)-2-cyclopentene-1-methanol

Conditions	Yield
In tetrahydrofuran; ethanol at 120℃; for 1h; Microwave irradiation;	13 mg

Upstream product

• 116477-30-6 4,6-dichloro-2,5-diformamido-pyrimidine 
• 122-51-0 orthoformic acid triethyl ester 
• 171887-04-0 (1R,4S)-1-[(2-amino-6-chloro-5-formamido-4-pyrimidinyl)amino]-4-(hydroxymethyl)-2-cyclopentene 
• 171887-02-8 2-amino-5-{[(dimethylamino)methylene]amino}-4,6-dichloropyrimidine 
• 171887-03-9 N-(2-amino-4,6-dichloropyrimidin-5-yl)formamide 
• 136522-35-5 (1R,4S)-1-amino-4-hydroxymethyl-2-cyclopentene 
• 79200-56-9 (-)-2-azabicyclo[2.2.1]hept-5-en-3-one 

Downstream Products

• 136470-78-5 abacavir 
• 124752-25-6 (1α,4α)-4-(2,6-Diamino-9H-purin-9-yl)-2-cyclopentenyl-carbinol 
• 136522-33-3 (1S,4R)-4-[2-amino-6-chloro-9H-purin-9-yl]-2-cyclopentene-1-methanol 

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