13276-52-3

Basic information

• Product Name: 2,6-Dichloropurine riboside
• Synonyms: 2, 6-DICHLOROPURINE RIBOSIDE (2,6DClPR);2,6-Dichloropurine r;2,6-Dichloro-9-β-D-ribofuranosyl-9H-purine;2,6-dichloropuine nuceotide;(2R,3R,4S,5R)-2-(2,6-Dichloro-9H-purin-9-yl)-5-(hydroxyMethyl)tetrahydrofuran-3,4-diol;2,6-dichloro-9-(β-D-ribofuranosyl)purine;2,6-Dichloro-9-(beta-D-ribofuranosyl)purine;2,6-Dichloropurine riboside###13276-52-3
• CAS NO: 13276-52-3
• Molecular Formula: C₁₀H₁₀Cl₂N₄O₄
• Molecular Weight: 321.1168
• EINECS: 1308068-626-2
• Product Categories: Bases & Related Reagents;Nucleotides;Miscellaneous Biochemicals;API intermediates
• Mol File: 13276-52-3.mol
• Article Data: 8

Chemical Properties

• Melting Point: >190°C (dec)
• Boiling Point: 589.3 °C at 760 mmHg
• Flash Point: 310.2 °C
• Appearance: white to off-white solid
• Density: 2.14 g/cm³
• Vapor Pressure: 9.86E-15mmHg at 25°C
• Refractive Index: 1.854
• Storage Temp.: Refrigerator
• Solubility: DMSO (Slightly), Methanol (Slightly), Water
• PKA: 13.00±0.70(Predicted)
• CAS DataBase Reference: 2,6-Dichloropurine riboside(CAS DataBase Reference)
• NIST Chemistry Reference: 2,6-Dichloropurine riboside(13276-52-3)
• EPA Substance Registry System: 2,6-Dichloropurine riboside(13276-52-3)

Safety Data

• Hazardous Substances Data: 13276-52-3(Hazardous Substances Data)

Usage

Chemical Properties

White to Off-White Solid

Uses

2,6-Dichloropurine-9-β-D-riboside is a useful reagent for the design of AB680 as potent and selective inhibitor of CD73.

InChI:InChI=1/C10H10Cl2N4O4/c11-7-4-8(15-10(12)14-7)16(2-13-4)9-6(19)5(18)3(1-17)20-9/h2-3,5-6,9,17-19H,1H2

Synthetic route

(2R,3R,4R,5R)-4-(acetyloxy)-2-[(acetyloxy)methyl]-5-(2,6-dichloro-9H-purin-9-yl)tetrahydro-3-furanyl acetate (3056-18-6) → 2,6-dichloropurine riboside (13276-52-3)

Conditions	Yield
With acetyl chloride In methanol at 0 - 10℃; for 1.5h; Inert atmosphere;	85%
With ammonia In methanol at 100℃; for 24h; Autoclave;
With methanol; sodium methylate at 25℃; for 5h; Temperature;	300 g

6-Chloro-2-nitro-9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-9H-purine (266360-68-3) → 2,6-dichloropurine riboside (13276-52-3)

Conditions	Yield
With hydrogenchloride In ethanol at 20℃; for 10h;	82%

(2R,3R,4R,5R)-2-((benzoyloxy)methyl)-5-(2,6-dichloro-9H-purin-9-yl)tetrahydrofuran-3,4-diyl dibenzoate (15373-23-6) → 2,6-dichloropurine riboside (13276-52-3)

Conditions	Yield
With acetyl chloride In methanol at 0 - 10℃; for 4h; Inert atmosphere;	82%

2,6 dichloropurine (5451-40-1) + uridine (58-96-8) → 2,6-dichloropurine riboside (13276-52-3)

Conditions	Yield
With potassium phosphate; Geobacillus thermoglucosidasius purine nucleoside phosphorylase; Geobacillus thermoglucosidasius pyrimidine nucleoside phosphorylase In water at 65℃; for 0.5h; pH=7; Reagent/catalyst; Enzymatic reaction;

2,6 dichloropurine (5451-40-1) + (3R,45,5R)-5-(((4-methoxyphenyl)diphenylmethoxy)methyl)tetrahydrofuran-2,3,4-triol → 2,6-dichloropurine riboside (13276-52-3)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 0.25 h / 20 °C / Inert atmosphere 1.2: 12 h / 0 - 20 °C / Inert atmosphere 2.1: hydrogenchloride / water; acetonitrile / 0.25 h / 60 °C / pH Ca. 1 / Inert atmosphere View Scheme

C30H26Cl2N4O5 → 2,6-dichloropurine riboside (13276-52-3)

Conditions	Yield
With hydrogenchloride In water; acetonitrile at 60℃; for 0.25h; pH=Ca. 1; Inert atmosphere;	94 mg

1,2,3,5-tetraacetylribose (13035-61-5) → 2,6-dichloropurine riboside (13276-52-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: tin(IV) chloride / 0.25 h / 90 - 120 °C 2: ammonia / methanol / 24 h / 100 °C / Autoclave View Scheme
Multi-step reaction with 2 steps 1: dmap / toluene / 2 h / 100 °C 2: sodium methylate; methanol / 5 h / 25 °C View Scheme

2,6 dichloropurine (5451-40-1) → 2,6-dichloropurine riboside (13276-52-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: tin(IV) chloride / 0.25 h / 90 - 120 °C 2: ammonia / methanol / 24 h / 100 °C / Autoclave View Scheme

2,6 dichloropurine (5451-40-1) + uridine (58-96-8) → uracil (66-22-8) + 2,6-dichloropurine riboside (13276-52-3)

Conditions	Yield
With potassium phosphate at 40℃; for 6h; pH=7.5; Equilibrium constant; Enzymatic reaction;	A n/a B 34 mg

2,6-dichloro-7H-purine (5451-40-1) → 2,6-dichloropurine riboside (13276-52-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: dmap / toluene / 2 h / 100 °C 2: sodium methylate; methanol / 5 h / 25 °C View Scheme

2,2-dimethoxy-propane (77-76-9) + 2,6-dichloropurine riboside (13276-52-3) → [(3aR,4R,6R,6aR)-4-(2,6-dichloropurin-9-yl)-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-6-yl]methanol (52678-40-7)

Conditions	Yield
With toluene-4-sulfonic acid In acetone at 20℃; for 16h;	94%

4-aminomethylphenol (696-60-6) + 2,6-dichloropurine riboside (13276-52-3) → 2-chloro-N6-(4-hydroxybenzyl)adenosine

Conditions	Yield
With triethylamine In butan-1-ol at -5 - 90℃;	92%

2,6-dichloropurine riboside (13276-52-3) → 2-Amino-6-chloropurine riboside (2004-07-1)

Conditions	Yield
With ammonia at 25℃; for 12h; Temperature;	90.3%

3-hydroxybenzylamine (73604-31-6) + 2,6-dichloropurine riboside (13276-52-3) → 2-chloro-N6-(3-hydroxybenzyl)adenosine (23559-61-7)

Conditions	Yield
With triethylamine In butan-1-ol at -5 - 90℃;	90%

acetone (67-64-1) + 2,6-dichloropurine riboside (13276-52-3) → [(3aR,4R,6R,6aR)-4-(2,6-dichloropurin-9-yl)-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-6-yl]methanol (52678-40-7)

Conditions	Yield
With toluene-4-sulfonic acid at 20℃; for 16h; Inert atmosphere;	90%

2-(aminomethyl)-6-methoxyphenol (86855-27-8) + 2,6-dichloropurine riboside (13276-52-3) → NGF1568

Conditions	Yield
With triethylamine In butan-1-ol at -5 - 90℃;	89%
With triethylamine In pentan-1-ol at 100℃; for 4h;

2-hydroxy-5-methylbenzylamine (65456-39-5) + 2,6-dichloropurine riboside (13276-52-3) → 2-chloro-N6-(2-hydroxy-5-methylbenzyl)adenosine (722524-59-6)

Conditions	Yield
With triethylamine In butan-1-ol at -5 - 90℃;	86%

3-METHOXYBENZYLAMINE (5071-96-5) + 2,6-dichloropurine riboside (13276-52-3) → 2-chloro-6-(3-methoxybenzylamino)purine riboside

Conditions	Yield
With triethylamine In butan-1-ol at 90℃; for 4h;	85%

2,2'-iminobis[ethanol] (111-42-2) + 2,6-dichloropurine riboside (13276-52-3) → 2-chloro-6-[N,N-bis(2-hydroxyethyl)amino]-9-(β-D-ribofuranosyl)purine (1181816-26-1)

Conditions	Yield
In water at 100℃; for 0.166667h; Microwave irradiation;	85%

Upstream product

• 5451-40-1 2,6-dichloro-7H-purine 
• 5451-40-1 2,6 dichloropurine 
• 58-96-8 uridine 
• 13035-61-5 1,2,3,5-tetraacetylribose 
• 15373-23-6 (2R,3R,4R,5R)-2-((benzoyloxy)methyl)-5-(2,6-dichloro-9H-purin-9-yl)tetrahydrofuran-3,4-diyl dibenzoate 
• 3056-18-6 (2R,3R,4R,5R)-4-(acetyloxy)-2-[(acetyloxy)methyl]-5-(2,6-dichloro-9H-purin-9-yl)tetrahydro-3-furanyl acetate 
• 266360-68-3 6-Chloro-2-nitro-9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-9H-purine 

Downstream Products

• 722527-50-6 2-chloro-6-(2,4-dimethylbenzylamino)purine riboside 
• 722515-52-8 2-chloro-6-(2,3-dihydroxybenzylamino)purine riboside 
• 722515-87-9 2-chloro-6-(2,5-dihydroxybenzylamino)purine riboside 
• 722522-13-6 2-chloro-6-(2-hydroxy-5-chlorobenzylamino)purine riboside 
• 722517-07-9 2-chloro-6-(2-methoxy-4-hydroxybenzylamino)purine riboside 
• 52678-40-7 [(3aR,4R,6R,6aR)-4-(2,6-dichloropurin-9-yl)-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-6-yl]methanol 
• 2004-07-1 2-Amino-6-chloropurine riboside 
• 149007-83-0 6-cyclopropylamino-2-chloro-9-(β-D-ribofuranosyl)purine 
• 23558-62-5 (2R,3R,4S,5R)-2-(6-(benzylamino)-2-chloro-9H-purin-9-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol 
• 15763-11-8 2-hydrazinoadenosine 
• 146-77-0 2-Chloroadenosine 
• 37739-05-2 2-chloro-N⁶-cyclopentyladenosine 
• 1254160-17-2 sodium ((2R,3S,4R,5R)-5-(2-chloro-6-(cyclohexylamino)-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl sulfate 
• 1338586-49-4 2-chloro-2',3'-isopropylidene-N⁶-cyclohexyladenosine 

Relevant articles and documents

Synthesis of 2,6-dihalogenated purine nucleosides by thermostable nucleoside phosphorylases

The enzymatic transglycosylation of 2,6-dichloropurine (26DCP) and 6-chloro-2-fluoropurine (6C2FP) with uridine, thymidine and 1-(β-D-arabinofuranosyl)-uracil as the pentofuranose donors and recombinant thermostable nucleoside phosphorylases from G. thermoglucosidasius or T. thermophilus as biocatalysts was studied. Selection of 26DCP and 6C2FP as substrates is determined by their higher solubility in aqueous buffer solutions compared to most natural and modified purines and, furthermore, synthesized nucleosides are valuable precursors for the preparation of a large number of biologically important nucleosides. The substrate activity of 26DCP and 6C2FP in the synthesis of their ribo- and 2′-deoxyribo-nucleosides was closely similar to that of related 2-amino- (DAP), 2-chloro- and 2-fluoroadenines; the efficiency of the synthesis of β-D-arabinofuranosides of 26DCP and 6C2FP was lower vs. that of DAP under similar reaction conditions. For a convenient and easier recovery of the biocatalysts, the thermostable enzymes were immobilized on MagReSyn epoxide beads and the biocatalyst showed high catalytic efficiency in a number of reactions. As an example, 6-chloro-2-fluoro-(β-D-ribofuranosyl)-purine (9), a precursor of various antiviral and antitumour drugs, was synthesized by the immobilized enzymes at 60°C under high substrate concentrations (uridine:purine ratio of 2:1, mol). The synthesis was successfully scaled-up [uridine (2.5 mmol), base (1.25 mmol); reaction mixture 50 mL] to afford 9 in 60% yield. The reaction reveals the great practical potential of this enzymatic method for the efficient production of modified purine nucleosides of pharmaceutical interest.

Intermediate for synthesizing 2-chloroadenosine, synthesis process of intermediate and synthesis process of 2-chloroadenosine

The invention relates to the technical field of organic synthesis, in particular to an intermediate for synthesizing 2-chloroadenosine, a synthesis process of the intermediate and a synthesis processof the 2-chloroadenosine. The synthesis process of the intermediate for synthesizing the 2-chloroadenosine comprises the following step: carrying out condensation reaction on 2,6-dichloropurine and tetraacetylribose under the catalytic action of 4-dimethylaminopyridine to form 2,3,5-4-triacetyl-2,6-dichloropurine riboside. The synthesis process is simple to operate, low in catalyst dosage, low incost, low in pollution and easy to industrially implement, and the yield and purity of the synthesized 2-chloroadenosine are higher.

A acyl-removing and protect the 2, 6 - position halogenated purine nucleoside method (by machine translation)

Invention discloses a deacylated and protect the 2, 6 - position halogenated purine nucleoside. In order to acetyl or benzoyl protection of 2, 6 - position halogenated purine nucleoside as raw materials, using acetyl chloride/alcohol system carries acetyl or benzoyl to obtain 2, 6 - position halogenated purine nucleoside, the method avoids the conventional method liquid ammonia/methanol or hydrochloric acid/methanol system, halogen atoms are amino or alkoxy substituted by-product, after treatment is simple, and high product purity, is suitable for industrial scale production. (by machine translation)