87-42-3

Basic information

• Product Name: 6-Chloropurine
• Synonyms: 1H-Purine, 6-chloro-;6-chloro-1h-purin;6-chloro-1h-purine;6-chloro-purin;6-Chlorpurine;ClP;NSC 744;nsc744
• CAS NO: 87-42-3
• Molecular Formula: C₅H₃ClN₄
• Molecular Weight: 154.56
• EINECS: 201-745-6
• Product Categories: FINE Chemical & INTERMEDIATES;Heterocyclic Compounds;Nucleotides and Nucleosides;Purines;Biochemistry;Nucleobases and their analogs;Nucleosides, Nucleotides & Related Reagents;Nucleic acids;Bases & Related Reagents;Nucleotides;Building Blocks;Halogenated Heterocycles;Heterocyclic Building Blocks;PurinesHeterocyclic Building Blocks;NucleosidesHeterocyclic Building Blocks;Biochemicals and Reagents;Nucleosides, Nucleotides, Oligonucleotides;Intermediates & Fine Chemicals;Pharmaceuticals;Building Blocks;Chemical Synthesis;Halogenated Heterocycles;Heterocyclic Building Blocks;Biochemicals and Reagents;Nucleosides;Oligonucleotides
• Mol File: 87-42-3.mol
• Article Data: 15

Chemical Properties

• Melting Point: >300 °C (dec.)(lit.)
• Boiling Point: 254.17°C (rough estimate)
• Flash Point: 258.2 °C
• Appearance: yellow-orange/crystalline
• Density: 1.4649 (rough estimate)
• Vapor Pressure: 0.0242mmHg at 25°C
• Refractive Index: 1.8430 (estimate)
• Storage Temp.: 2-8°C
• Solubility: 5 g/L
• PKA: 7.47±0.20(Predicted)
• Water Solubility: 5 g/L
• Merck: 14,2161
• BRN: 5774
• CAS DataBase Reference: 6-Chloropurine(CAS DataBase Reference)
• NIST Chemistry Reference: 6-Chloropurine(87-42-3)
• EPA Substance Registry System: 6-Chloropurine(87-42-3)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 22-36/37/38-20/21/22
• Safety Statements: 26-36-36/37/39
• WGK Germany: 3
• RTECS: UO7520000
• F: 10-23
• HazardClass: IRRITANT
• Hazardous Substances Data: 87-42-3(Hazardous Substances Data)

Usage

Chemical Properties

White crystals

Uses

Different sources of media describe the Uses of 87-42-3 differently. You can refer to the following data:
1. 6-Chloropurine is used in the preparation of 9-alkylpurines through alkylation with various substituted alkyl halides in dimethyl sulfoxide. It is also used to prepare 6-succinoaminopurine.
2. 6-Chloropurine has been used in the preparation of:9-alkylpurines via alkylation with various substituted alkyl halides in DMSO6-succinoaminopurine

Synthesis Reference(s)

Journal of the American Chemical Society, 78, p. 1928, 1956 DOI: 10.1021/ja01590a043

General Description

The acid-catalyzed reaction of 6-chloropurine with 3,4-di-O-acetyl-D-xylal has been investigated.

Purification Methods

6-Chloropurine crystallises from water. The UV in water at pH 1 has 264nm (log 3.94). [Beilstein 26 III/IV 1742.]

InChI:InChI=1/C5H3ClN4/c6-4-3-5(9-1-7-3)10-2-8-4/h1-3H

Synthetic route

4,5,6-trichloropyrimidine (1780-27-4) + formimidamide hydrochloride → 6-chloropurine (87-42-3)

Conditions	Yield
In ethanol at 15 - 25℃; for 12h;	97.1%

6-[2-(ethoxycarbonyl)methyl]-9-(tetrahydropyran-2-yl)-9H-purine (948037-39-6) → 6-chloropurine (87-42-3)

Conditions	Yield
With Dowex 50 In ethanol at 70℃; for 3h;	93%

hypoxanthine (68-94-0) → 6-chloropurine (87-42-3)

Conditions	Yield
With N,N-dimethyl-aniline; trichlorophosphate under 760.051 Torr; Heating;	92%
With trichlorophosphate In N,N-dimethyl acetamide at 120℃; for 2h;	86%
With trichlorophosphate In N,N-dimethyl-formamide at 80℃; for 8h;	76.7%
With trichlorophosphate In ethylbenzene; acetonitrile at 65℃; for 6h;	53%

Allopurinol (68-94-0) → 6-chloropurine (87-42-3)

Conditions	Yield
With dmap; thionyl chloride; bis(trichloromethyl) carbonate Catalytic behavior; Reagent/catalyst; Reflux; Green chemistry;	90%
With trichlorophosphate In dichloromethane; N,N-dimethyl-formamide at 40℃; for 3h;	71.5%
With 2,3-Dimethylaniline; trichlorophosphate for 0.5h; Heating;	47%

9-(3'-azido-2'-O-triflyl-5'-O-benzoyl-3'-deoxy-β-D-ribofuranosyl)-6-chloro-9H-purine (917239-31-7) → benzoic acid 3-azido-furan-2-ylmethyl ester + 6-chloropurine (87-42-3)

Conditions	Yield
With tetrabutyl ammonium fluoride In tetrahydrofuran at 20℃; for 20h;	A 84% B 82%

C20H30ClFN4O4Si (1062217-28-0) → C14H16ClFN4O4 + C11H12ClFN4O4 (1062217-43-9) + 6-chloropurine (87-42-3)

Conditions	Yield
With trifluoroacetic acid In 1,4-dioxane for 7h;	A n/a B 41% C n/a

C20H30ClFN4O4Si (1062217-31-5) → C11H12ClFN4O4 (1062217-44-0) + C14H16ClFN4O4 (1062217-36-0) + 6-chloropurine (87-42-3)

Conditions	Yield
With trifluoroacetic acid In 1,4-dioxane for 7h;	A 37% B n/a C n/a

9-(1-Ethoxyethyl-1)-6-chloropurine (33441-77-9) → 6-chloropurine (87-42-3)

Conditions	Yield
In hydrogenchloride; water at 40.1℃; Kinetics; Mechanism;

6-chloropurine-2'-deoxyriboside (4594-45-0) → 6-chloropurine (87-42-3)

Conditions	Yield
In hydrogenchloride; water at 50.1℃; Kinetics; Mechanism;

9-(3'-azido-5'-O-benzoyl-3'-deoxy-β-D-ribofuranosyl)-6-chloro-9H-purine (917239-30-6) → 6-chloropurine (87-42-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: 84 percent / pyridine / CH2Cl2 / -40 °C 2: 82 percent / TBAF / tetrahydrofuran / 20 h / 20 °C View Scheme

xanthine (69-89-6) → 6-chloropurine (87-42-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: 70 percent / formamide / 0.5 h / 200 °C 2: 53 percent / POCl3 / ethylbenzene; acetonitrile / 6 h / 65 °C View Scheme

Acetic acid (3S,4R)-4-acetoxy-2-chloro-tetrahydro-pyran-3-yl ester (87990-00-9) + 6-chloropurine (87-42-3) → Acetic acid (2R,3R,4S)-4-acetoxy-2-(6-chloro-purin-9-yl)-tetrahydro-pyran-3-yl ester (87990-01-0)

Conditions	Yield
With 3 A molecular sieve; Quecksilber(I)-cyanid In nitromethane for 3h; Heating;	100%

6-chloropurine (87-42-3) + 1,2,3,5-tetra-O-benzoyl-2-C-methyl-β-D-ribofuranose (15397-15-6) → (2R,3R,4R,5R)-5-((benzoyloxy)methyl)-2-(6-chloro-9H-purin-9-yl)-3-methyltetrahydrofuran-3,4-diyl dibenzoate (205171-04-6)

Conditions	Yield
	100%
With trimethylsilyl trifluoromethanesulfonate; 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 60℃; for 4h;	83%
With benzenesulfonamide; trimethylsilyl trifluoromethanesulfonate In acetonitrile at 60℃; for 3h;
With trimethylsilyl trifluoromethanesulfonate; 1,8-diazabicyclo[5.4.0]undec-7-ene In tetrahydrofuran at 20℃; for 18h;

6-chloropurine (87-42-3) + Cyclopropylamine (765-30-0) → 6-(cyclopropylamino)-9H-purine (117761-02-1)

Conditions	Yield
In ethanol for 6h; Heating;	100%
In isopropyl alcohol at 120℃; for 2h;	90%
In methanol	81.4%
In ethanol Heating;
In ethanol for 16h; Heating;

morpholine (110-91-8) + 6-chloropurine (87-42-3) → 6-morpholinopurine (2846-96-0)

Conditions	Yield
With indium(III) chloride In acetonitrile at 120℃; for 0.5h; Microwave irradiation; regioselective reaction;	100%
at 80℃;	96%
at 80℃; for 0.0166667h; microwave irradiation;	94%

4-morpholino-4-yl-phenylamine (2524-67-6) + 6-chloropurine (87-42-3) → 6-(4-morpholinophenylamino)-9H-purin-3-ium chloride

Conditions	Yield
With indium(III) chloride In acetonitrile at 120℃; for 1h; Microwave irradiation; regioselective reaction;	100%

2-(hydroxy(phenyl)methyl)-4-methylphenol (55075-31-5) + 6-chloropurine (87-42-3) → C19H15ClN4O

Conditions	Yield
With toluene-4-sulfonic acid In dichloromethane at 20℃; for 6h;	100%

3,4-dihydro-2H-pyran (110-87-2) + 6-chloropurine (87-42-3) → 6-chloro-9-(tetrahydro-2H-pyran-2-yl)-9H-purine (7306-68-5)

Conditions	Yield
With toluene-4-sulfonic acid In ethyl acetate at 90℃; for 1h;	99%
With toluene-4-sulfonic acid In ethyl acetate at 90℃; for 1h;	99.3%
With toluene-4-sulfonic acid In ethyl acetate at 90℃; for 0.1h;	97%

phenylacetylene (536-74-3) + 6-chloropurine (87-42-3) → 6-(phenylethynyl)-9H-purine (85110-23-2)

Conditions	Yield
With sodium tetrachloropalladate(II); dicyclohexyl {2-sulfo-9-[3-(4-sulfophenyl)propyl]-9H-fluoren-9-yl}phosphonium hydrogen sulfate; potassium carbonate In water at 95℃; for 16h; Sonogashira coupling; Inert atmosphere;	99%
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine In dimethyl sulfoxide at 90℃; for 1.5h;	65%

sodium thiophenolate (930-69-8) + 6-chloropurine (87-42-3) → 6-(phenylsulfanyl)purine (5450-35-1)

Conditions	Yield
In N,N-dimethyl-formamide at 80℃; for 0.0166667h; microwave irradiation;	99%

sodium ethanolate (141-52-6) + 6-chloropurine (87-42-3) → 6-ethoxy-9H-purine (17861-06-2)

Conditions	Yield
In 1-methyl-pyrrolidin-2-one at 100℃; for 0.0333333h; microwave irradiation;	99%

6-chloropurine (87-42-3) + sodium thiomethoxide (5188-07-8) → 6-methylthiopurine (50-66-8)

Conditions	Yield
In N,N-dimethyl-formamide at 80℃; for 0.0166667h; microwave irradiation;	99%

Benzeneselenol (645-96-5) + 6-chloropurine (87-42-3) → 6-(phenylselanyl)-9H-purine

Conditions	Yield
With barium dihydroxide In water at 90℃; for 0.0333333h; microwave irradiation;	99%

sodium methylate (124-41-4) + 6-chloropurine (87-42-3) → 6-methoxypurine (1074-89-1)

Conditions	Yield
In N,N-dimethyl-formamide at 90℃; for 0.0166667h; microwave irradiation;	99%
In methanol for 18h; Reflux;	72%
In methanol for 12h; Reflux; Inert atmosphere;	43%

1-(hydroxymethyl)-4-propylpyrrolidin-2-one (854141-63-2) + 6-chloropurine (87-42-3) → 1-[(6-chloro-9H-purin-9-yl)methyl]-4-propylpyrrolidin-2-one (916257-23-3)

Conditions	Yield
N,N-diethylcarbamyl chloride In acetonitrile at 100℃; for 5h; Microwave;	99%

diphenyliodonium chloride (1483-72-3) + 6-chloropurine (87-42-3) → 6-Chloro-9-phenyl-9H-purine (5470-24-6)

Conditions	Yield
With potassium carbonate; copper(I) bromide In dichloromethane for 2.5h; Reflux; Inert atmosphere; regioselective reaction;	99%

hexan-1-amine (111-26-2) + 6-chloropurine (87-42-3) → N6-n-hexyladenine (14333-96-1)

Conditions	Yield
With indium(III) chloride In acetonitrile at 120℃; for 1.5h; Microwave irradiation; regioselective reaction;	99%

2-[hydroxy(4-methylphenyl)methyl]phenol + 6-chloropurine (87-42-3) → C19H15ClN4O

Conditions	Yield
With toluene-4-sulfonic acid In dichloromethane at 20℃; for 5h;	99%

para-thiocresol (106-45-6) + 6-chloropurine (87-42-3) → 6-(p-tolylthio)purine

Conditions	Yield
With potassium tert-butylate In isopropyl alcohol at 50℃;	98%

methyl N-trityl-L-serinate (13515-76-9, 116457-91-1, 4465-44-5) + 6-chloropurine (87-42-3) → methyl 3-(6-chloro-9H-purin-9-yl)-2-(tritylamino)propanoate (1228040-59-2)

Conditions	Yield
With di-isopropyl azodicarboxylate; triphenylphosphine In 5,5-dimethyl-1,3-cyclohexadiene at 25℃; for 1h; Mitsunobu reaction;	98%

2-(hydroxymethyl)-6-methyl-1,3,6,2-dioxazaborocane-4,8-dione + 6-chloropurine (87-42-3) → C11H11BClN5O4

Conditions	Yield
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 23℃; for 0.5h; Mitsunobu Displacement;	98%

4-carboxamidopiperidine (39546-32-2) + 6-chloropurine (87-42-3) → 1-(9H-purin-6-yl)piperidine-4-carboxylic acid amide

Conditions	Yield
With triethylamine In butan-1-ol at 100℃;	97%
With triethylamine In butan-1-ol at 100℃; for 0.666667h;

trityl chloride (76-83-5) + 6-chloropurine (87-42-3) → 6-chloro-9-trityl-9H-purine (1008361-76-9)

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 2h; Inert atmosphere;	97%

aniline (62-53-3) + 6-chloropurine (87-42-3) → 6-(phenylamino)-9H-purin-3-ium chloride

Conditions	Yield
With indium(III) chloride In acetonitrile at 120℃; for 0.5h; Microwave irradiation; regioselective reaction;	97%

3-((trimethylsilyl)oxy)propan-1-amine hydrochloride + 6-chloropurine (87-42-3) → N6-(3-hydroxypropyl)adenine (15500-81-9)

Conditions	Yield
With potassium carbonate In tetrahydrofuran; N,N-dimethyl-formamide at 70℃; for 72h; Reagent/catalyst; Solvent; Temperature; Inert atmosphere;	97%

4-hydroxy-3-methyl-trans-but-2-enylamine (1795-76-2, 26806-03-1, 35042-70-7) + 6-chloropurine (87-42-3) → trans-zeatin (1637-39-4)

Conditions	Yield
With triethylamine In ethanol for 5h; Reflux;	96.8%
With triethylamine In butan-1-ol for 3h; Heating;	80%

3-methyl-2-butenamide (4479-75-8) + 6-chloropurine (87-42-3) → 3-methyl-but-2-enoic acid 7(9)H-purin-6-ylamide (21589-34-4)

Conditions	Yield
With triethylamine In ethanol for 5h; Reflux;	96.8%

furan-2-ylmethanamine (617-89-0) + 6-chloropurine (87-42-3) → kinetin (525-79-1)

Conditions	Yield
With triethylamine In ethanol for 5h; Reflux;	96.7%
In ethanol Reflux; Inert atmosphere;	88%
With triethylamine In butan-1-ol at 110℃; for 5h;	76.4%
With triethylamine In butan-1-ol at 110℃;	73.9%
With N-ethyl-N,N-diisopropylamine In butan-1-ol at 100℃; for 16h;

3,3-dimethylallylamine (13822-06-5, 108963-90-2) + 6-chloropurine (87-42-3) → N6-(2-isopentenyl)adenine (2365-40-4)

Conditions	Yield
With triethylamine In ethanol for 5h; Reflux;	96.6%

6-chloropurine (87-42-3) → adenine (66224-66-6, 66224-67-7, 66224-68-8, 66224-69-9, 134434-48-3, 134434-49-4, 134454-76-5, 134461-75-9)

Conditions	Yield
With ammonium hydroxide; triethylamine In ethanol for 5h; Reflux;	96.3%
With potassium amide In ammonia at -33℃; for 20h; Yield given;
Multi-step reaction with 3 steps 1: potassium carbonate / N,N-dimethyl-formamide / 17 h / 20 °C / Inert atmosphere 2: ammonia / tert-butyl alcohol / 21 h / 120 °C 3: potassium carbonate / 7 h / 200 °C / Microwave irradiation View Scheme

Upstream product

• 4594-45-0 6-chloropurine-2'-deoxyriboside 
• 68-94-0 hypoxanthine 
• 1780-27-4 4,5,6-trichloropyrimidine 
• 1062217-31-5 C₂₀H₃₀ClFN₄O₄Si 
• 1062217-28-0 C₂₀H₃₀ClFN₄O₄Si 
• 69-89-6 xanthine 
• 917239-30-6 9-(3'-azido-5'-O-benzoyl-3'-deoxy-β-D-ribofuranosyl)-6-chloro-9H-purine 
• 948037-39-6 6-[2-(ethoxycarbonyl)methyl]-9-(tetrahydropyran-2-yl)-9H-purine 
• 917239-31-7 9-(3'-azido-2'-O-triflyl-5'-O-benzoyl-3'-deoxy-β-D-ribofuranosyl)-6-chloro-9H-purine 
• 68-94-0 Allopurinol 
• 33441-77-9 9-(1-Ethoxyethyl-1)-6-chloropurine 
• 67-56-1 methanol 
• 7782-50-5 chlorine 
• 50-66-8 6-(methylthio)-1H-purine 

Downstream Products

• 525-79-1 kinetin 
• 1928-81-0 6-(piperidin-1-yl)purine 
• 525-81-5 (7(9)H-purin-6-yl)-[2]thienylmethyl-amine 
• 13268-73-0 6-(2-methylbenzylamino)purine 
• 88166-55-6 dodecyl-(7⁽⁹⁾H-purin-6-yl)-amine 
• 36412-32-5 octyl-(7(9)H-purin-6-yl)-amine 
• 6288-93-3 6-n-propylthiopurine 
• 26511-42-2 N-(7(9)H-purin-6-yl)-L-aspartic acid 
• 5069-82-9 6-n-butylthiopurine 
• 5443-89-0 6-pentylmercapto-7⁽⁹⁾H-purine 
• 37109-78-7 6-hexylmercapto-7⁽⁹⁾H-purine 
• 14814-48-3 heptyl-(7(9)H-purin-6-yl)-amine 
• 18917-30-1 6-(7(9)H-purin-6-ylamino)-hexan-1-ol 
• 5270-30-4 1,7-dihydro-purine-6-selone 

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