28020-38-4

Basic information

• Product Name: 2,3-Diamino-6-methoxypyridine
• Synonyms: 2,3-DIAMINO-6-METHOXYPYRIDINE HCL;2,3-DIAMINO-6-METHOXYPYRIDINE HYDROCHLORIDE;2,3-diamino-6-methoxpyridine;2,3-Diamino-6-methoxypyridine hydrochloride 98%;2,3-Diamino-6-methoxypyridine;2,3-Diamino-6-methoxypyridine Hydrochlor
• CAS NO: 28020-38-4
• Molecular Formula: C₆H₉N₃O
• Molecular Weight: 139.16
• EINECS: 207-166-5
• Product Categories: Pyridines derivates;Pyridine
• Mol File: 28020-38-4.mol
• Article Data: 21

Chemical Properties

• Melting Point: 168-170°C
• Boiling Point: 321.7 °C at 760 mmHg
• Flash Point: 148.3 °C
• Appearance: /
• Density: 1.251 g/cm³
• Vapor Pressure: 4.13E-05mmHg at 25°C
• Storage Temp.: 2-8°C(protect from light)
• PKA: 4.55±0.50(Predicted)
• CAS DataBase Reference: 2,3-Diamino-6-methoxypyridine(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3-Diamino-6-methoxypyridine(28020-38-4)
• EPA Substance Registry System: 2,3-Diamino-6-methoxypyridine(28020-38-4)

Safety Data

• Hazard Codes: Xi
• Statements: 20/21/22-36/37/38
• Safety Statements: 26-36/37/39-36
• Hazardous Substances Data: 28020-38-4(Hazardous Substances Data)

Usage

General Description

2,3-Diamino-6-methoxypyridine is a chemical compound with the molecular formula C6H9N3O. It is a derivative of pyridine and contains two amino groups and a methoxy group. 2,3-Diamino-6-methoxypyridine is commonly used in the synthesis of pharmaceuticals and agrochemicals, and it has also been found to have potential applications in the field of organic chemistry. 2,3-Diamino-6-methoxypyridine is known for its ability to act as a chelating agent, forming coordination compounds with metal ions, which makes it useful in catalysis and as a ligand in metal-organic frameworks. Additionally, it has been studied for its potential biological activities and is being researched for its potential use in medicinal applications.

InChI:InChI=1/C6H9N3O.ClH/c1-10-5-3-2-4(7)6(8)9-5;/h2-3H,7H2,1H3,(H2,8,9);1H

Synthetic route

6-methoxy-3-nitropyridin-2-amine (73896-36-3) → 2,3-diamino-6-methoxypyridine (28020-38-4)

Conditions	Yield
With palladium on activated charcoal; hydrogen In methanol at 20℃; for 16h;	100%
With hydrogen; palladium 10% on activated carbon at 25℃; for 6h;	99%
With hydrogen; palladium on activated charcoal In ethanol under 760 Torr;

6-methoxypyridine-2,3-diamine dihydrochloride → 2,3-diamino-6-methoxypyridine (28020-38-4)

Conditions	Yield
With ammonia In water at 15℃; pH=7 - 8;	92%

2-amino-6-chloro-3-nitropyridine (27048-04-0) → 2,3-diamino-6-methoxypyridine (28020-38-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: 70 percent / NaOMe / 2 h / Heating 2: H2 / 10percent Pd/C / ethanol / 760 Torr View Scheme
Multi-step reaction with 2 steps 1: ethanol / 16 h / -15 - 20 °C 2: hydrogenchloride; tin(ll) chloride / 5 h / 50 °C View Scheme

2,6-dicholoro-3-nitropyridine (16013-85-7) → 2,3-diamino-6-methoxypyridine (28020-38-4)

Conditions	Yield
Multi-step reaction with 3 steps 1: ammonium hydroxide / 5 h / 50 °C 2: ethanol / 16 h / -15 - 20 °C 3: hydrogenchloride; tin(ll) chloride / 5 h / 50 °C View Scheme

2,6-dichloropyridine (2402-78-0) → 2,3-diamino-6-methoxypyridine (28020-38-4)

Conditions	Yield
Multi-step reaction with 4 steps 1: sulfuric acid; nitric acid / -15 - 150 °C 2: ammonium hydroxide / 5 h / 50 °C 3: ethanol / 16 h / -15 - 20 °C 4: hydrogenchloride; tin(ll) chloride / 5 h / 50 °C View Scheme

2-chloro-6-methoxy-3-nitropyridine (38533-61-8) → 2,3-diamino-6-methoxypyridine (28020-38-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: ammonia / methanol / 18 h / 65 °C 2: hydrogen / palladium on activated charcoal / ethanol / 20 °C / 760.05 Torr View Scheme
Multi-step reaction with 2 steps 1: ammonia; ammonium hydroxide / methanol / 18 h / 65 °C 2: hydrogen; palladium on activated charcoal / ethanol / 760.05 Torr View Scheme

2,3-diamino-6-methoxypyridine (28020-38-4) + 4-cyanobenzaldehyde (105-07-7) → 2-(4-cyanophenyl)-5-methoxy-4-azabenzimidazole

Conditions	Yield
With sodium metabisulfite; dimethyl sulfoxide at 165℃; for 0.25h; Inert atmosphere; Sealed tube;	92%

5-(3,4,5-trimethoxybenzoyl)-1H-indole-3-carbaldehyde + 2,3-diamino-6-methoxypyridine (28020-38-4) → (3-(5-cethoxy-3H-imidazo[4,5-b]pyridin-2-yl)-1H-indol-5-yl)(3,4,5-trimethoxyphenyl)methanone

Conditions	Yield
With sodium metabisulfite In ethanol; water at 80℃; for 2h;	85%

2,3-diamino-6-methoxypyridine (28020-38-4) + benzyl chloroformate (501-53-1) → benzyl 2-amino-6-methoxypyridin-3-ylcarbamate (1040363-61-8)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In dichloromethane at 0℃; for 1h;	83%

formic acid (64-18-6) + 2,3-diamino-6-methoxypyridine (28020-38-4) → 5-methoxy-1H-imidazo[4,5-b]pyridine

Conditions	Yield
at 105℃; for 8h;	78.6%

1-methyl-5-(3,4,5-trimethoxybenzoyl)-1H-indole-3-carbaldehyde (1427690-73-0) + 2,3-diamino-6-methoxypyridine (28020-38-4) → (3-(5-methoxy-3H-imidazo[4,5-b]pyridin-2-yl)-1-methyl-1H-indol-5-yl)(3,4,5-trimethoxyphenyl)methanone

Conditions	Yield
With sodium metabisulfite In ethanol; water at 80℃; for 2h;	73%

C21H21NO5 + 2,3-diamino-6-methoxypyridine (28020-38-4) → (1-ethyl-3-(5-methoxy-3H-imidazo[4,5-b]pyridin-2-yl)-1H-indol-5-yl)(3,4,5-trimethoxyphenyl)methanone

Conditions	Yield
With sodium metabisulfite In ethanol; water at 80℃; for 2h;	72%

1-(trifluoroacetyl)-4-piperidone (65220-86-2) + 2,3-diamino-6-methoxypyridine (28020-38-4) → 1-(4-(2-amino-6-methoxypyridin-3-ylamino)piperidin-1-yl)-2,2,2-trifluoroethanone (1040363-59-4)

Conditions	Yield
With sodium tris(acetoxy)borohydride In chloroform at 25℃; for 3h;	70%

2-methoxy-4-(methylsulfanyl)benzoic acid (72856-73-6) + 2,3-diamino-6-methoxypyridine (28020-38-4) → 5-Methoxy-2-(2-methoxy-4-methylsulfanyl-phenyl)-1H-imidazo[4,5-b]pyridine (127356-18-7)

Conditions	Yield
With trichlorophosphate 1.) RT, 0.5 h, 2.) reflux, 6 h;	52%

2,3-diamino-6-methoxypyridine (28020-38-4) + 1,1'-carbonyldiimidazole (530-62-1) → 5-methoxy-1H-imidazo[4,5-b]pyridin-2(3H)-one (1388046-13-6)

Conditions	Yield
With triethylamine In tetrahydrofuran at 20℃; for 2h; Inert atmosphere;	31%

2,3-diamino-6-methoxypyridine (28020-38-4) + ethyl 2-cyanoacetate (105-56-6) → 2-(5-methoxy-3H-imidazo[4,5-b]pyridin-2-yl)acetonitrile

Conditions	Yield
In N,N-dimethyl-formamide at 180℃; for 5h;	22.2%

glyoxylic acid ethyl ester (924-44-7) + 2,3-diamino-6-methoxypyridine (28020-38-4) → 6-methoxypyrido[2,3-b]pyrazin-2(1H)-one + 6-methoxy-4H-pyrido[2,3-b]pyrazin-3-one (917344-37-7)

Conditions	Yield
In methanol at 20℃;	A n/a B 13%

oxalic acid (144-62-7) + 2,3-diamino-6-methoxypyridine (28020-38-4) → 6-methoxy-1,4-dihydropyrido[2,3-b]pyrazine-2,3-dione (144435-07-4)

Conditions	Yield
With hydrogenchloride Heating; Yield given;

2,3-diamino-6-methoxypyridine (28020-38-4) → 6-Hydroxy-1,4-dihydro-pyrido[2,3-b]pyrazine-2,3-dione

Conditions	Yield
Multi-step reaction with 2 steps 1: 4N aq. HCl / Heating 2: 70 percent / 48percent aq. HBr / 4 h / Heating View Scheme

2,3-diamino-6-methoxypyridine (28020-38-4) → 6-Methoxy-7-nitro-1,4-dihydro-pyrido[2,3-b]pyrazine-2,3-dione

Conditions	Yield
Multi-step reaction with 2 steps 1: 4N aq. HCl / Heating 2: 62 percent / AcOH, Ac2O, HNO3 / 1 h / 90 °C View Scheme

2,3-diamino-6-methoxypyridine (28020-38-4) → 2-(4-Methanesulfinyl-2-methoxy-phenyl)-5-methoxy-1H-imidazo[4,5-b]pyridine (127356-01-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: 52 percent / POCl3 / 1.) RT, 0.5 h, 2.) reflux, 6 h 2: 53 percent / m-chloroperbenzoic acid / CHCl3 / 1.5 h / -15 °C View Scheme

N-tert-butyloxycarbonylpiperidin-4-one (79099-07-3) + 2,3-diamino-6-methoxypyridine (28020-38-4) → 2-amino-3-[(1-tert-butoxycarbonylpiperidin-4-yl)amino]-6-methoxypyridine

Conditions	Yield
Stage #1: N-tert-butyloxycarbonylpiperidin-4-one; 2,3-diamino-6-methoxypyridine With sodium tris(acetoxy)borohydride In 1,2-dichloro-ethane at 20℃; Stage #2: With sodium hydroxide In water; 1,2-dichloro-ethane

pyrazolo[1,5-a]pyridin-3-ylamine (137837-55-9) + 2,3-diamino-6-methoxypyridine (28020-38-4) → C19H15N9

Conditions	Yield
With dihydrogen peroxide In ethanol; water at 20℃; for 168h; pH=7;

2-ethyl-5-methyl-2H-3,4-diaminopyrazole (184172-99-4) + 2,3-diamino-6-methoxypyridine (28020-38-4) → C17H25N11

Conditions	Yield
With sodium hydroxide; ammonium cerium(IV) nitrate In water; acetonitrile for 4h;

2,4,5,6-tetraaminopyrimidine (1004-74-6) + 2,3-diamino-6-methoxypyridine (28020-38-4) → C13H17N15

Conditions	Yield
With sodium hydroxide; ammonium cerium(IV) nitrate In water; acetonitrile for 4h;

3-amino-7-dimethylaminopyrazolopyrimidine + 2,3-diamino-6-methoxypyridine (28020-38-4) → C21H23N13

Conditions	Yield
With dihydrogen peroxide In ethanol; water at 20℃; for 168h;

2,3-diamino-6-methoxypyridine (28020-38-4) + ethyl bromoacetate (105-36-2) → 6-(methyloxy)-1,4-dihydropyrido[2,3-b]pyrazin-3(2H)-one (1073633-84-7) + ethyl N-[2-amino-6-(methyloxy)-3-pyridinyl]glycinate (1073633-83-6)

Conditions	Yield
With potassium carbonate In acetonitrile at 20℃;
With potassium carbonate In acetonitrile at 20℃; Inert atmosphere;	A 15 %Spectr. B 75 %Spectr.
With potassium carbonate In acetonitrile at 20℃; Product distribution / selectivity;

2,3-diamino-6-methoxypyridine (28020-38-4) + ethyl bromoacetate (105-36-2) → ethyl N-[2-amino-6-(methyloxy)-3-pyridinyl]glycinate (1073633-83-6)

Conditions	Yield
With potassium carbonate In acetonitrile at 20℃;
With potassium carbonate In acetonitrile at 20℃; Inert atmosphere;

carbon disulfide (75-15-0) + 2,3-diamino-6-methoxypyridine (28020-38-4) → 5-methoxy-1,3-dihydro-2H-imidazo[4,5-b]pyridine-2-thione (113713-60-3)

Conditions	Yield
Stage #1: carbon disulfide; 2,3-diamino-6-methoxypyridine With sodium hydroxide In ethanol Reflux; Stage #2: With hydrogenchloride In ethanol	0.187 g
With potassium hydroxide In ethanol; water at 80℃;
With potassium hydroxide In ethanol; water for 12h; Reflux;	16.9 g
With potassium hydroxide In water at 70℃;

3-(4-methoxypyridin-2-yl) propionic acid (608880-87-1) + 2,3-diamino-6-methoxypyridine (28020-38-4) → C15H16N4O2 (608880-52-0)

Conditions	Yield
With polyphosphoric acid at 110 - 160℃;

2,3-diamino-6-methoxypyridine (28020-38-4) → 4-(2-{4-[(2,3-dihydro[1,4]dioxino[2,3-c]pyridin-7-ylmethyl)amino]piperidin-1-yl}ethyl)-6-methoxypyrido[2,3-b]pyrazin-3(4H)-one

Conditions	Yield
Multi-step reaction with 5 steps 1.1: methanol / 20 °C 2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0 - 20 °C 2.2: 20 °C 3.1: trifluoroacetic acid / dichloromethane / 0.5 h / 0 °C 4.1: methanol; chloroform / 3 h / 70 °C / Molecular sieve 5.1: sodium tris(acetoxy)borohydride / methanol; chloroform / 0 - 20 °C View Scheme

2,3-diamino-6-methoxypyridine (28020-38-4) → C23H26N6O4

Conditions	Yield
Multi-step reaction with 4 steps 1.1: methanol / 20 °C 2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0 - 20 °C 2.2: 20 °C 3.1: trifluoroacetic acid / dichloromethane / 0.5 h / 0 °C 4.1: methanol; chloroform / 3 h / 70 °C / Molecular sieve View Scheme

Upstream product

• 73896-36-3 6-methoxy-3-nitropyridin-2-amine 
• 38533-61-8 2-chloro-6-methoxy-3-nitropyridine 
• 2402-78-0 2,6-dichloropyridine 
• 16013-85-7 2,6-dicholoro-3-nitropyridine 
• 1159824-73-3 6-methoxypyridine-2,3-diamine dihydrochloride 
• 27048-04-0 2-amino-6-chloro-3-nitropyridine 

Downstream Products

• 1438246-37-7 C₂₄H₂₃N₅O₄ 
• 1438246-06-0 C₂₄H₂₃N₅O₄ 
• 1073634-29-3 phenylmethyl 6-(methyloxy)-3-oxo-3,4-dihydropyrido[2,3-b]pyrazine-1(2H)-carboxylate 
• 1073634-23-7 4-(3-amino-3,4-dihydro-2H-pyrano[3,2-b]pyridin-7-yl)-6-(methyloxy)-1,4-dihydropyrido[2,3-b]pyrazin-3(2H)-one 
• 1073634-24-8 6-(methyloxy)-4-(3-{[(phenylmethyl)oxy]amino}-3,4-dihydro-2H-pyrano[3,2-b]pyridin-7-yl)-1,4-dihydropyrido[2,3-b]pyrazin-3(2H)-one 
• 1073634-22-6 6-(methyloxy)-4-(3-{[(phenylmethyl)oxy]amino}-3,4-dihydro-2H-pyrano[3,2-b]pyridin-7-yl)pyrido[2,3-b]pyrazin-3(4H)-one 
• 1073633-91-6 phenylmethyl 4-[6-({[(1,1-dimethylethyl)oxy]carbonyl}amino)-5,6,7,8-tetrahydro-2-quinazolinyl]-6-(methyloxy)-3-oxo-3,4-dihydropyrido[2,3-b]pyrazine-1(2H)-carboxylate 
• 1096666-10-2 5-methoxy-1H-imidazo[4,5-b]pyridine 
• 1075234-83-1 (1R)-1-({4-[([1,3]oxathiolo[5,4-c]pyridin-6-ylmethyl)amino]-1-piperidinyl}methyl)-1,2-dihydro-3H,8H-2a,5,8a-triazaacenaphthylene-3,8-dione benzoate 
• 1075237-89-6 phenylmethyl (1R)-1-{[4-({[(1,1-dimethylethyl)oxy]carbonyl}amino)-1-piperidinyl]methyl}-3,8-dioxo-1,2,3,4-tetrahydro-5H,8H-2a,5,8a-triazaacenaphthylene-5-carboxylate 
• 1075237-88-5 phenylmethyl (1S)-1-{[(methylsulfonyl)oxy]methyl}-3,8-dioxo-1,2,3,4-tetrahydro-5H,8H-2a,5,8a-triazaacenaphthylene-5-carboxylate 
• 1075237-80-7 phenylmethyl (1S)-1-(hydroxymethyl)-3,8-dioxo-1,2,3,4-tetrahydro-5H,8H-2a,5,8a-triazaacenaphthylene-5-carboxylate 
• 1388144-49-7 ethyl (1-{5-[3-chloro-4-(5-methoxy-3H-imidazo[4,5-b]pyridin-2-yl)phenyl]pyridin-2-yl}piperidin-4-yl)acetate 

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