2589-12-0

Basic information

• Product Name: 4,6-DICHLOROIMIDAZO[4,5-C]PYRIDINE
• Synonyms: 4,6-DICHLOROIMIDAZO[4,5-C]PYRIDINE;2,6-Dichloro-3-deazapurine;4,6-dichloro-1H-imidazo[4,5-c]pyridine;4,6-Dichloro-3H-imidazo[4,5-c]pyridine;5-c]pyridine;6-dichloro-1H-iMidazo[4;3H-IMidazo[4,5-c]pyridine, 4,6-dichloro-;NSC 264047
• CAS NO: 2589-12-0
• Molecular Formula: C₆H₃Cl₂N₃
• Molecular Weight: 188.01412
• Product Categories: Nucleotides and Nucleosides;CHIRAL CHEMICALS;Bases & Related Reagents;Nucleotides;Heterocycle-Pyridine series
• Mol File: 2589-12-0.mol
• Article Data: 6

Chemical Properties

• Melting Point: 253-254°C
• Boiling Point: 482.902 °C at 760 mmHg
• Flash Point: 277.938 °C
• Appearance: Beige solid
• Density: 1.675 g/cm³
• Vapor Pressure: 5.15E-09mmHg at 25°C
• Refractive Index: 1.723
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility: DMSO (Slightly), Methanol (Slightly, Heated)
• PKA: 6.55±0.40(Predicted)
• CAS DataBase Reference: 4,6-DICHLOROIMIDAZO[4,5-C]PYRIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 4,6-DICHLOROIMIDAZO[4,5-C]PYRIDINE(2589-12-0)
• EPA Substance Registry System: 4,6-DICHLOROIMIDAZO[4,5-C]PYRIDINE(2589-12-0)

Safety Data

• Hazardous Substances Data: 2589-12-0(Hazardous Substances Data)

Usage

Chemical Properties

Beige Solid

InChI:InChI=1/C6H3Cl2N3/c7-4-1-3-5(6(8)11-4)10-2-9-3/h1-2H,(H,9,10)

Synthetic route

3,4-diamino-2,6-dichloropyridine (101079-63-4) + orthoformic acid triethyl ester (122-51-0) → 4,6-dichloro-1H-imidazo<4,5-c>pyridine (2589-12-0)

Conditions	Yield
With acetic anhydride for 4.5h; Heating;	96%
Stage #1: 3,4-diamino-2,6-dichloropyridine; orthoformic acid triethyl ester With acetic anhydride for 4.5h; Reflux; Stage #2: With sodium hydroxide In water at 50℃; for 0.666667h;
Stage #1: 3,4-diamino-2,6-dichloropyridine; orthoformic acid triethyl ester With acetic anhydride at 90℃; for 4.5h; Stage #2: With sodium hydroxide In water at 85 - 90℃; for 0.75h;	3.4 g

3,4-diamino-2,6-dichloropyridine dihydrochloride + orthoformic acid triethyl ester (122-51-0) → 4,6-dichloro-1H-imidazo<4,5-c>pyridine (2589-12-0)

Conditions	Yield
With acetic anhydride at 145℃; for 0.5h;	90%

3-amino-4-acetamido-2,6-dichloropyridine (668268-66-4) → 4,6-dichloro-1H-imidazo<4,5-c>pyridine (2589-12-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: aq. NaOH / Heating 2: 96 percent / Ac2O / 4.5 h / Heating View Scheme

2,6-dichloropyridine (2402-78-0) → 4,6-dichloro-1H-imidazo<4,5-c>pyridine (2589-12-0)

Conditions	Yield
Multi-step reaction with 8 steps 1: CF3COOH; aq. H2O2 / 6.5 h / Heating 2: HNO3; H2SO4 / 160 °C 3: AcOH; Fe / Heating 4: HNO3; H2SO4 / 20 °C 5: H2SO4 / 100 °C 6: 51 percent / Fe / 2 h / Heating 7: aq. NaOH / Heating 8: 96 percent / Ac2O / 4.5 h / Heating View Scheme
Multi-step reaction with 7 steps 1: CF3COOH; aq. H2O2 / 6.5 h / Heating 2: HNO3; H2SO4 / 160 °C 3: AcOH; Fe / Heating 4: HNO3; H2SO4 / 20 °C 5: H2SO4 / 100 °C 6: 94 percent / Fe; H2O; HCl / ethanol / 16 h / 95 °C 7: 96 percent / Ac2O / 4.5 h / Heating View Scheme

2,6-dichloro-[4]pyridylamine (2587-02-2) → 4,6-dichloro-1H-imidazo<4,5-c>pyridine (2589-12-0)

Conditions	Yield
Multi-step reaction with 5 steps 1: HNO3; H2SO4 / 20 °C 2: H2SO4 / 100 °C 3: 51 percent / Fe / 2 h / Heating 4: aq. NaOH / Heating 5: 96 percent / Ac2O / 4.5 h / Heating View Scheme
Multi-step reaction with 4 steps 1: HNO3; H2SO4 / 20 °C 2: H2SO4 / 100 °C 3: 94 percent / Fe; H2O; HCl / ethanol / 16 h / 95 °C 4: 96 percent / Ac2O / 4.5 h / Heating View Scheme

2,6-dichloropyridine N-oxide (2587-00-0) → 4,6-dichloro-1H-imidazo<4,5-c>pyridine (2589-12-0)

Conditions	Yield
Multi-step reaction with 7 steps 1: HNO3; H2SO4 / 160 °C 2: AcOH; Fe / Heating 3: HNO3; H2SO4 / 20 °C 4: H2SO4 / 100 °C 5: 51 percent / Fe / 2 h / Heating 6: aq. NaOH / Heating 7: 96 percent / Ac2O / 4.5 h / Heating View Scheme
Multi-step reaction with 6 steps 1: HNO3; H2SO4 / 160 °C 2: AcOH; Fe / Heating 3: HNO3; H2SO4 / 20 °C 4: H2SO4 / 100 °C 5: 94 percent / Fe; H2O; HCl / ethanol / 16 h / 95 °C 6: 96 percent / Ac2O / 4.5 h / Heating View Scheme

2,6-dichloro-N-nitro-4-pyridinamine (2587-03-3) → 4,6-dichloro-1H-imidazo<4,5-c>pyridine (2589-12-0)

Conditions	Yield
Multi-step reaction with 4 steps 1: H2SO4 / 100 °C 2: 51 percent / Fe / 2 h / Heating 3: aq. NaOH / Heating 4: 96 percent / Ac2O / 4.5 h / Heating View Scheme
Multi-step reaction with 3 steps 1: H2SO4 / 100 °C 2: 94 percent / Fe; H2O; HCl / ethanol / 16 h / 95 °C 3: 96 percent / Ac2O / 4.5 h / Heating View Scheme
Multi-step reaction with 3 steps 1.1: sulfuric acid / 1 h / 100 °C 2.1: hydrogen / methanol / 4 h 3.1: acetic anhydride / 4.5 h / 90 °C 3.2: 0.75 h / 85 - 90 °C View Scheme

2,6-dichloro-3-nitropyridin-4-amine (2897-43-0) → 4,6-dichloro-1H-imidazo<4,5-c>pyridine (2589-12-0)

Conditions	Yield
Multi-step reaction with 3 steps 1: 51 percent / Fe / 2 h / Heating 2: aq. NaOH / Heating 3: 96 percent / Ac2O / 4.5 h / Heating View Scheme
Multi-step reaction with 2 steps 1: 94 percent / Fe; H2O; HCl / ethanol / 16 h / 95 °C 2: 96 percent / Ac2O / 4.5 h / Heating View Scheme
Multi-step reaction with 3 steps 1: iron; hydrogenchloride / water; ethanol / 16 h / Reflux 2: 5 h / 145 °C 3: formic acid / 5 h / 110 °C View Scheme
Multi-step reaction with 2 steps 1.1: hydrogen / methanol / 4 h 2.1: acetic anhydride / 4.5 h / 90 °C 2.2: 0.75 h / 85 - 90 °C View Scheme

2,6-dichloro-4-nitro-pyridine (25194-01-8) → 4,6-dichloro-1H-imidazo<4,5-c>pyridine (2589-12-0)

Conditions	Yield
Multi-step reaction with 6 steps 1: AcOH; Fe / Heating 2: HNO3; H2SO4 / 20 °C 3: H2SO4 / 100 °C 4: 51 percent / Fe / 2 h / Heating 5: aq. NaOH / Heating 6: 96 percent / Ac2O / 4.5 h / Heating View Scheme
Multi-step reaction with 5 steps 1: AcOH; Fe / Heating 2: HNO3; H2SO4 / 20 °C 3: H2SO4 / 100 °C 4: 94 percent / Fe; H2O; HCl / ethanol / 16 h / 95 °C 5: 96 percent / Ac2O / 4.5 h / Heating View Scheme

3,4-diamino-2,6-dichloropyridine (101079-63-4) → 4,6-dichloro-1H-imidazo<4,5-c>pyridine (2589-12-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: 5 h / 145 °C 2: formic acid / 5 h / 110 °C View Scheme

C8H9Cl2N3O → 4,6-dichloro-1H-imidazo<4,5-c>pyridine (2589-12-0)

Conditions	Yield
With formic acid at 110℃; for 5h;	390 mg

3,4-dihydro-2H-pyran (110-87-2) + 4,6-dichloro-1H-imidazo<4,5-c>pyridine (2589-12-0) → 4,6-dichloro-1-(tetrahydro-2H-pyran-2-yl)-1H-imidazo[4,5-c]pyridine

Conditions	Yield
With toluene-4-sulfonic acid In dichloromethane at 20℃; for 3h;	91%
With toluene-4-sulfonic acid In tetrahydrofuran Reflux;	55%

4,6-dichloro-1H-imidazo<4,5-c>pyridine (2589-12-0) + 1,2,3,5-tetraacetylribose (13035-61-5) → 2,6-dichloro-9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-3-deazapurine (63423-94-9)

Conditions	Yield
Heating;	90%
With toluene-4-sulfonic acid at 160℃; for 0.166667h; stereoselective reaction;	76%

4,6-dichloro-1H-imidazo<4,5-c>pyridine (2589-12-0) + (2S,3R,5S)-5-((benzoyloxy)methyl)tetrahydrofuran-2,3-diyl diacetate (90580-88-4) → benzoic acid 4-acetoxy-5-(4,6-dichloro-imidazo[4,5-c]pyridin-1-yl)-tetrahydro-furan-2-ylmethyl ester

Conditions	Yield
With toluene-4-sulfonic acid Heating;	90%

4,6-dichloro-1H-imidazo<4,5-c>pyridine (2589-12-0) + benzyl alcohol (100-51-6) → 2-benzyloxy-7-chloropyrido[4,5-c]imidazole (52559-19-0)

Conditions	Yield
With sodium at 120℃;	85%

4,6-dichloro-1H-imidazo<4,5-c>pyridine (2589-12-0) + (2R,3R,4R,5R)-5-(benzoyloxymethyl)-3-methyltetrahydrofuran-2,3,4-triyl tribenzoate → C33H25Cl2N3O7 (1254180-69-2)

Conditions	Yield
With trimethylsilyl trifluoromethanesulfonate; 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 60℃; for 3h;	70%

4,6-dichloro-1H-imidazo<4,5-c>pyridine (2589-12-0) + (2S,3R,5S)-5-((benzoyloxy)methyl)tetrahydrofuran-2,3-diyl diacetate (90580-88-4) → 1-(2-O-acetyl-5-O-benzoyl-3-deoxy-β-D-ribofuranosyl)-4,6-dichloro-1H-imidazo<4,5-c>pyridine (220249-14-9) + 1-(2-O-acetyl-5-O-benzoyl-3-deoxy-α-D-ribofuranosyl)-4,6-dichloro-1H-imidazo<4,5-c>pyridine + 1-(2-O-acetyl-5-O-benzoyl-3-deoxy-α-D-arabinofuranosyl)-4,6-dichloro-1H-imidazo<4,5-c>pyridine

Conditions	Yield
With toluene-4-sulfonic acid at 160℃; under 25 Torr; for 0.166667h;	A 52% B 24% C 14%
With toluene-4-sulfonic acid at 160℃; for 0.166667h; Substitution;

4,6-dichloro-1H-imidazo<4,5-c>pyridine (2589-12-0) + (2S,3R,5S)-5-((benzoyloxy)methyl)tetrahydrofuran-2,3-diyl diacetate (90580-88-4) → 4,6-dichloro-1-(3-deoxy-β-D-ribofuranosyl)-1H-imidazo<4,5-c>pyridine (220249-17-2) + 4,6-dichloro-1-(3-deoxy-α-D-ribofuranosyl)-1H-imidazo<4,5-c>pyridine (220249-18-3) + 4,6-dichloro-1-(3-deoxy-α-D-arabinofuranosyl)-1H-imidazo<4,5-c>pyridine + (2R,3S,5S)-2-(4,6-Dichloro-imidazo[4,5-c]pyridin-1-yl)-5-hydroxymethyl-tetrahydro-furan-3-ol

Conditions	Yield
Stage #1: 4,6-dichloro-1H-imidazo<4,5-c>pyridine; (2S,3R,5S)-5-((benzoyloxy)methyl)tetrahydrofuran-2,3-diyl diacetate With toluene-4-sulfonic acid Heating; Stage #2: With ammonia In methanol	A 51% B 23% C 13% D 3%

(3aR,3bR,4aS,5S,5aS)-3b-(((tert-butyldiphenylsilyl)oxy)methyl)-2,2-dimethylhexahydrocyclopropa[3,4]cyclopenta[1,2-d][1,3]dioxol-5-ol (915694-38-1) + 4,6-dichloro-1H-imidazo<4,5-c>pyridine (2589-12-0) → 1-((3aR,3bR,4aS,5R,5aS)-3b-(((tert-butyldiphenylsilyl)oxy)methyl)-2,2-dimethylhexahydrocyclopropa[3,4]cyclopenta[1,2-d][1,3]dioxol-5-yl)-4,6-dichloro-1H-imidazo[4,5-c]pyridine

Conditions	Yield
Stage #1: 4,6-dichloro-1H-imidazo<4,5-c>pyridine With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 0 - 20℃; for 0.333333h; Stage #2: (3aR,3bR,4aS,5S,5aS)-3b-(((tert-butyldiphenylsilyl)oxy)methyl)-2,2-dimethylhexahydrocyclopropa[3,4]cyclopenta[1,2-d][1,3]dioxol-5-ol In tetrahydrofuran at 20℃;	50%
Stage #1: 4,6-dichloro-1H-imidazo<4,5-c>pyridine With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 0 - 20℃; for 0.333333h; Stage #2: (3aR,3bR,4aS,5S,5aS)-3b-(((tert-butyldiphenylsilyl)oxy)methyl)-2,2-dimethylhexahydrocyclopropa[3,4]cyclopenta[1,2-d][1,3]dioxol-5-ol In tetrahydrofuran at 20℃;	50%

4,6-dichloro-1H-imidazo<4,5-c>pyridine (2589-12-0) → 2-chloro-3-deazaadenine (52559-17-8)

Conditions	Yield
With ammonia In methanol at 160℃; for 90h;	49%
With ammonia In methanol at 160℃; for 90h;

2,3,5-tri-O-benzyl-α- and β-D-arabinofuranosyl chlorides (52554-29-7) + 4,6-dichloro-1H-imidazo<4,5-c>pyridine (2589-12-0) → 3-((3S,4R,5R)-3,4-Bis-benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-yl)-4,6-dichloro-3H-imidazo[4,5-c]pyridine + 4,6-dichloro-1-(2,3,5-tri-O-benzyl-β-D-arabinofuranosyl)imidazo<4,5-c>pyridine (80161-98-4) + 4,6-dichloro-1-(2,3,5-tri-O-benzyl-α-D-arabinofuranosyl)imidazo<4,5-c>pyridine (80161-98-4)

Conditions	Yield
With 4 A molecular sieve In 1,2-dichloro-ethane Heating; Yield given;	A n/a B 37% C n/a
With 4 A molecular sieve In 1,2-dichloro-ethane Heating; Yields of byproduct given;	A n/a B 37% C n/a

4,6-dichloro-1H-imidazo<4,5-c>pyridine (2589-12-0) + (2S,3R,5S)-5-((benzoyloxy)methyl)tetrahydrofuran-2,3-diyl diacetate (90580-88-4) → 1-(2-O-acetyl-5-O-benzoyl-3-deoxy-β-D-ribofuranosyl)-4,6-dichloro-1H-imidazo<4,5-c>pyridine (220249-14-9)

Conditions	Yield
With tin(IV) chloride In acetonitrile	27%

2-deoxy-3,5-di-O-p-toluoyl-α-D-erythro-pentofuranosyl chloride (4330-21-6) + 4,6-dichloro-1H-imidazo<4,5-c>pyridine (2589-12-0) → 4,6-dichloro-1-(2-deoxy-3,5-di-O-p-toluoyl-β-D-erythro-pentofuranosyl)imidazo<4,5-c>pyridine (91713-45-0)

Conditions	Yield
With sodium hydride 1.) acetonitrile, r.t., 30 min; 2.) 50 deg C, 2 h; Yield given. Multistep reaction;

4,6-dichloro-1H-imidazo<4,5-c>pyridine (2589-12-0) + (2S,3R,5S)-5-((benzoyloxy)methyl)tetrahydrofuran-2,3-diyl diacetate (90580-88-4) → 4,6-dichloro-1-(3-deoxy-β-D-ribofuranosyl)-1H-imidazo<4,5-c>pyridine (220249-17-2) + 4,6-dichloro-1-(3-deoxy-α-D-ribofuranosyl)-1H-imidazo<4,5-c>pyridine (220249-18-3) + 4,6-dichloro-1-(3-deoxy-α-D-arabinofuranosyl)-1H-imidazo<4,5-c>pyridine

Conditions	Yield
With ammonia; toluene-4-sulfonic acid 1.) neat, 160 deg C, 25 Torr, 5-10 min, 2.) MeOH, rt, 24 h; Yield given; Multistep reaction. Yields of byproduct given;

4,6-dichloro-1H-imidazo<4,5-c>pyridine (2589-12-0) + (2S,3R,5S)-5-((benzoyloxy)methyl)tetrahydrofuran-2,3-diyl diacetate (90580-88-4) → 1-(2-O-acetyl-5-O-benzoyl-3-deoxy-β-D-ribofuranosyl)-4,6-dichloro-1H-imidazo<4,5-c>pyridine (220249-14-9) + 1-(2-O-acetyl-5-O-benzoyl-3-deoxy-α-D-ribofuranosyl)-4,6-dichloro-1H-imidazo<4,5-c>pyridine + 1-(2-O-acetyl-5-O-benzoyl-3-deoxy-α-D-arabinofuranosyl)-4,6-dichloro-1H-imidazo<4,5-c>pyridine + Benzoic acid (2S,4S,5R)-4-acetoxy-5-(4,6-dichloro-imidazo[4,5-c]pyridin-1-yl)-tetrahydro-furan-2-ylmethyl ester

Conditions	Yield
With toluene-4-sulfonic acid Heating;

4,6-dichloro-1H-imidazo<4,5-c>pyridine (2589-12-0) → 8-chloro-3-deazaadenine

Conditions	Yield
Multi-step reaction with 3 steps 1: 49 percent / ammonia / methanol / 90 h / 160 °C 2: 72 percent / NaOH; H2 / Pd/C / H2O / 20 h / 1758.3 Torr 3: 31 percent / t-butyl hypochlorite / dimethylsulfoxide / 144 h / 20 °C View Scheme
Multi-step reaction with 3 steps 1: 49 percent / ammonia / methanol / 90 h / 160 °C 2: 72 percent / NaOH; H2 / Pd/C / H2O / 20 h / 1758.3 Torr 3: HCl; mCPBA / N,N-dimethyl-acetamide / 0.42 h / 20 °C View Scheme

4,6-dichloro-1H-imidazo<4,5-c>pyridine (2589-12-0) → 3-chloro-3-deazaadenine

Conditions	Yield
Multi-step reaction with 3 steps 1: 49 percent / ammonia / methanol / 90 h / 160 °C 2: 72 percent / NaOH; H2 / Pd/C / H2O / 20 h / 1758.3 Torr 3: 6.2 percent / HCl; mCPBA / N,N-dimethyl-acetamide / 0.42 h / 20 °C View Scheme

4,6-dichloro-1H-imidazo<4,5-c>pyridine (2589-12-0) → 2,8-dichloro-3-deazaadenine

Conditions	Yield
Multi-step reaction with 2 steps 1: 49 percent / ammonia / methanol / 90 h / 160 °C 2: 38 percent / HCl; mCPBA / N,N-dimethyl-acetamide / 20 °C View Scheme

4,6-dichloro-1H-imidazo<4,5-c>pyridine (2589-12-0) → 3-deazaadenine (6811-77-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: 49 percent / ammonia / methanol / 90 h / 160 °C 2: 72 percent / NaOH; H2 / Pd/C / H2O / 20 h / 1758.3 Torr View Scheme

Upstream product

• 101079-63-4 3,4-diamino-2,6-dichloropyridine 
• 122-51-0 orthoformic acid triethyl ester 
• 668268-66-4 3-amino-4-acetamido-2,6-dichloropyridine 
• 2402-78-0 2,6-dichloropyridine 
• 2587-02-2 2,6-dichloro-[4]pyridylamine 
• 2587-00-0 2,6-dichloropyridine N-oxide 
• 2587-03-3 2,6-dichloro-N-nitro-4-pyridinamine 
• 2897-43-0 2,6-dichloro-3-nitropyridin-4-amine 
• 25194-01-8 4-nitro-2,6-dichloro-pyridine 
• 149-73-5 trimethyl orthoformate 

Downstream Products

• 91713-45-0 4,6-dichloro-1-(2-deoxy-3,5-di-O-p-toluoyl-β-D-erythro-pentofuranosyl)imidazo<4,5-c>pyridine 
• 80161-98-4 4,6-dichloro-1-(2,3,5-tri-O-benzyl-β-D-arabinofuranosyl)imidazo<4,5-c>pyridine 
• 80161-98-4 4,6-dichloro-1-(2,3,5-tri-O-benzyl-α-D-arabinofuranosyl)imidazo<4,5-c>pyridine 
• 220249-14-9 1-(2-O-acetyl-5-O-benzoyl-3-deoxy-β-D-ribofuranosyl)-4,6-dichloro-1H-imidazo<4,5-c>pyridine 
• 63423-94-9 2,6-dichloro-9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-3-deazapurine 
• 52559-17-8 2-chloro-3-deazaadenine 
• 668268-64-2 8-chloro-3-deazaadenine 
• 668268-69-7 3-chloro-3-deazaadenine 
• 6811-77-4 3-deazaadenine 
• 80161-97-3 4-amino-6-chloro-1-(2,3,5-tri-O-benzyl-β-D-arabinofuranosyl)imidazo<4,5-c>pyridine 
• 52559-19-0 4-(benzyloxy)-6-chloro-3H-imidazo[4,5-c]pyridine 
• 1254180-69-2 C₃₃H₂₅Cl₂N₃O₇ 
• 579486-43-4 6-benzyloxy-7-(4-methoxybutyl)-4-chloroimidazo[4,5-c]pyridine 
• 579486-44-5 6-benzyloxy-7-(5-methoxypentyl)-4-chloroimidazo[4,5-c]pyridine 

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