13754-19-3

Basic information

• Product Name: 4,5-Diaminopyrimidine
• Synonyms: PYRIMIDINE-4,5-DIAMINE;4,5-Pyrimidinediamine (9CI);4,5-DIAMIOPYRIMIDINE;4,5-DIAMINOPYRIMIDINE 98%;4,5-DIAMINOPYRIMIDINE 96% Minimum;4,5-Diaminopyrimidine ,97%;4,5-Diaminopyrimidiine;(4-aminopyrimidin-5-yl)amine
• CAS NO: 13754-19-3
• Molecular Formula: C₄H₆N₄
• Molecular Weight: 110.12
• EINECS: 237-339-0
• Product Categories: PYRIMIDINE;APIs & Intermediate;Pyrimidine series;Building Blocks;Heterocyclic Building Blocks;Pyrimidines;Building Blocks;C4 to C5;Chemical Synthesis;Heterocyclic Building Blocks
• Mol File: 13754-19-3.mol

Chemical Properties

• Melting Point: 204-206 °C(lit.)
• Boiling Point: 229 °C32 mm Hg(lit.)
• Flash Point: 175.8 °C
• Appearance: Clear colorless/Liquid
• Density: 1.2105 (rough estimate)
• Vapor Pressure: 4.94E-05mmHg at 25°C
• Refractive Index: 1.7380 (estimate)
• Storage Temp.: -20°C
• PKA: 6.06±0.10(Predicted)
• BRN: 112646
• CAS DataBase Reference: 4,5-Diaminopyrimidine(CAS DataBase Reference)
• NIST Chemistry Reference: 4,5-Diaminopyrimidine(13754-19-3)
• EPA Substance Registry System: 4,5-Diaminopyrimidine(13754-19-3)

Safety Data

• WGK Germany: 3
• F: 10
• Hazardous Substances Data: 13754-19-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
4,5-Diaminopyrimidine is used as an intermediate in the synthesis of Nisin, a natural preservative with potent antibacterial activity against gram-positive bacteria. This application is particularly valuable in the development of antibiotics and preservation techniques for the pharmaceutical and food industries.
Used in Chemical Synthesis:
4,5-Diaminopyrimidine is used as a reagent for synthesizing uracil-based 2-aminoanilide derivatives. These compounds exhibit histone deacetylase inhibitory properties, making them valuable in the development of therapeutic agents for various diseases, particularly those involving epigenetic regulation.

InChI:InChI=1/C4H6N4/c5-3-1-7-2-8-4(3)6/h1-2H,5H2,(H2,6,7,8)

Synthetic route

2-chloro-4,5-diaminopyrimidine (14631-08-4) → 4,5-pyrimidinediamine (13754-19-3)

6-chloro-4,5-diaminopyrimidine (4316-98-7) → 4,5-pyrimidinediamine (13754-19-3)

Conditions	Yield
With palladium on activated charcoal; water Hydrogenation;

4,5-diamino-1H-pyrimidine-2-thione (14623-58-6) → 4,5-pyrimidinediamine (13754-19-3)

Conditions	Yield
With ammonia; water; nickel

4-amino-2-chloro-5-nitropyrimidine (1920-66-7) → 4,5-pyrimidinediamine (13754-19-3)

Conditions	Yield
With hydrogen iodide at 0℃; anschliessend Behandeln unter Zusatz von Phosphoniumjodid bei 50grad;

4-amino-5-formamidopyrimidine (16008-45-0) → 4,5-pyrimidinediamine (13754-19-3) + purine (120-73-0)

Conditions	Yield
With sodium hydroxide at 70.1℃; Rate constant; different hydroxide ion concentrations;

4-amino-5-formamidopyrimidine (16008-45-0) → 4,5-pyrimidinediamine (13754-19-3) + formic acid (64-18-6) + purine (120-73-0)

Conditions	Yield
With perchloric acid at 90.1℃; Rate constant; Mechanism; Thermodynamic data; prod. yield/prod. distrib.; other temperatures, other reagent, ΔS(excit.), pH influence, phosphate buffer influence;

(2R,3R,4R,5R)-2-(5-Amino-pyrimidin-4-ylamino)-tetrahydro-pyran-3,4,5-triol (93135-56-9) → 4,5-pyrimidinediamine (13754-19-3) + D-Ribose (532-20-7, 613-83-2, 7261-25-8, 7687-39-0, 13221-22-2, 14795-83-6, 15761-67-8, 20074-49-1, 25545-03-3, 25545-04-4, 32445-75-3, 34436-17-4, 36441-93-7, 36468-53-8, 37110-85-3, 37388-49-1, 38029-69-5, 40461-77-6, 40461-89-0, 41546-19-4, 41546-20-7, 41546-21-8, 41546-26-3, 41546-29-6, 41546-30-9, 41546-31-0, 126872-16-0, 131064-98-7)

Conditions	Yield
With sodium hydroxide at 70.1℃; Kinetics; Mechanism; other temperatures and different hydroxide ion concentrations;

(3aR,4R,7R,7aR)-4-(5-Amino-pyrimidin-4-ylamino)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-ol → 4,5-pyrimidinediamine (13754-19-3) + 2,3-O-isopropylidene-D-ribofuranose (67814-68-0, 70266-87-4, 76249-50-8, 76249-51-9, 93451-15-1, 4099-88-1)

Conditions	Yield
With sodium hydroxide at 60.1℃; Rate constant; different hydroxide ion concentrations;

C8(14)CH14N4O4 → 4,5-pyrimidinediamine (13754-19-3) + <1-14C>-D-ribose (19214-82-5)

Conditions	Yield
With sodium hydroxide at 70.1℃; Rate constant; Mechanism;

9-(1-methoxyethyl)purine (95103-63-2) → 4,5-pyrimidinediamine (13754-19-3) + 2-methylbenzoimidazole (934-33-8) + 7,8-dihydro-8-methylpurine

Conditions	Yield
With sodium hydroxide at 70.1℃; Rate constant;

9-(1-ethoxyethyl)-9H-purine (78105-09-6) → 4,5-pyrimidinediamine (13754-19-3) + 2-methylbenzoimidazole (934-33-8)

Conditions	Yield
With sodium hydroxide In water at 60.1℃; Product distribution; Rate constant; other temperatures; alkalyne hydrolysis of 6-substituted 9-(1-ethoxyethyl)purines, effect of substituent, formation of intermediates;

9-(1-ethoxyethyl)-9H-purine (78105-09-6) → 4,5-pyrimidinediamine (13754-19-3) + 2-methylbenzoimidazole (934-33-8) + 7,8-dihydro-8-methylpurine

Conditions	Yield
With sodium hydroxide at 70.1℃; Rate constant;

9-(1-Isopropoxy-ethyl)-9H-purine (95103-62-1) → 4,5-pyrimidinediamine (13754-19-3) + 2-methylbenzoimidazole (934-33-8) + 7,8-dihydro-8-methylpurine

Conditions	Yield
With sodium hydroxide at 70.1℃; Rate constant;

9-[1-(2-Chloro-ethoxy)-ethyl]-9H-purine (95103-65-4) → 4,5-pyrimidinediamine (13754-19-3) + 2-methylbenzoimidazole (934-33-8) + 7,8-dihydro-8-methylpurine

Conditions	Yield
With sodium hydroxide at 70.1℃; Rate constant;

9-[1-(2-Methoxy-ethoxy)-ethyl]-9H-purine → 4,5-pyrimidinediamine (13754-19-3) + 2-methylbenzoimidazole (934-33-8) + 7,8-dihydro-8-methylpurine

Conditions	Yield
With sodium hydroxide at 70.1℃; Rate constant;

9-(1-ethoxy<2'-(3)H>ethyl)purine → 4,5-pyrimidinediamine (13754-19-3) + C6H5(3)HN4 + C6H7(3)HN4

Conditions	Yield
With sodium hydroxide at 70.1℃; Rate constant;

C8(14)CH12N4O → 4,5-pyrimidinediamine (13754-19-3) + 2-methylbenzoimidazole (934-33-8) + 7,8-dihydro-8-methylpurine

Conditions	Yield
With sodium hydroxide at 70.1℃; Rate constant;

Nebularin (550-33-4) → 4,5-pyrimidinediamine (13754-19-3) + D-Ribose (532-20-7, 613-83-2, 7261-25-8, 7687-39-0, 13221-22-2, 14795-83-6, 15761-67-8, 20074-49-1, 25545-03-3, 25545-04-4, 32445-75-3, 34436-17-4, 36441-93-7, 36468-53-8, 37110-85-3, 37388-49-1, 38029-69-5, 40461-77-6, 40461-89-0, 41546-19-4, 41546-20-7, 41546-21-8, 41546-26-3, 41546-29-6, 41546-30-9, 41546-31-0, 126872-16-0, 131064-98-7) + purine (120-73-0)

Conditions	Yield
With perchloric acid at 90.1℃; Rate constant; Mechanism; Thermodynamic data; prod. yield/prod. distrib.; other temperatures, other reagent, ΔS(excit.), pH influence;

Nebularin (550-33-4) + aqueous Ba(OH)2 → 4,5-pyrimidinediamine (13754-19-3)

4-amino-2-chloro-5-nitropyrimidine (1920-66-7) + hydrogen iodide (10034-85-2) + phosphonium iodide → 4,5-pyrimidinediamine (13754-19-3)

4,5-pyrimidinediamine (13754-19-3) + formic acid (64-18-6) → purine (120-73-0)

Conditions	Yield
With orthoformic acid triethyl ester at 90℃; for 3.5h;	100%

4,5-pyrimidinediamine (13754-19-3) + trifluoroacetic acid (76-05-1) → 8-(trifluoromethyl)-9H-purine (2268-12-4)

Conditions	Yield
at 70℃; for 16h;	99%

4,5-pyrimidinediamine (13754-19-3) + 4-benzoyl-3-hydroxy-2,5-dihydrofuran-2-one (7478-57-1) → 2<(4-amino-5-pyrimidinyl)amine>-4-oxo-3-(hydroxymethyl)-4-phenyl-2-butenoic acid (86475-08-3)

Conditions	Yield
In ethanol Ambient temperature; overnight;	95%

4,5-pyrimidinediamine (13754-19-3) + 2-methoxy-4-(methylsulfanyl)benzoic acid (72856-73-6) → 8-(2-Methoxy-4-methylsulfanyl-phenyl)-9H-purine; hydrochloride (95420-69-2)

Conditions	Yield
With trichlorophosphate for 4h; Heating;	91%

4,5-pyrimidinediamine (13754-19-3) + 2,3,4,5,6-penta-O-acetyl-D-gluconyl isothiocyanate (58314-42-4) → Acetic acid (1S,2R,3R,4R)-2,3,4,5-tetraacetoxy-1-(4-thioxo-4,5-dihydro-3H-pyrimido[4,5-f][1,3,5]triazepin-2-yl)-pentyl ester (61169-10-6)

Conditions	Yield
In tetrahydrofuran; benzene at 70 - 85℃;	90%

4,5-pyrimidinediamine (13754-19-3) + carbon monoxide (201230-82-2) → 7H-purin-8(9H)-one (13230-97-2)

Conditions	Yield
With selenium In dimethyl sulfoxide at 100℃; under 22800.7 Torr; for 20h;	89%
With selenium 1.) DMF, 31 kg/cm2, 100 degC, 20 h, 2.) 25 degC, 1 h;	87%

4,5-pyrimidinediamine (13754-19-3) + o-fluoro-benzoic acid (445-29-4) → 8-(2-fluorophenyl)-purine (878287-56-0)

Conditions	Yield
Stage #1: 4,5-pyrimidinediamine; o-fluoro-benzoic acid With polyphosphoric acid at 180℃; for 3h; Stage #2: With sodium hydroxide In water pH=8 - 9;	88.5%

4,5-pyrimidinediamine (13754-19-3) + cyclohexyl-phenyl-acetyl chloride (49802-71-3) → N-(5-aminopyrimidin-4-yl)-2-cyclohexyl-2-phenylacetamide (897446-49-0)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 12h;	88%

4,5-pyrimidinediamine (13754-19-3) + dimethyl N-(1,3-benzothiazol-2-yl) dithio imidocarbonate (76423-99-9) → 8-(2-benzothiazolylamino)-purine (103588-19-8)

Conditions	Yield
In various solvent(s) Heating;	86%

4,5-pyrimidinediamine (13754-19-3) + 2-hydroxynaphthalene-1-carbaldehyde (708-06-5) → 1-[(4-aminopyrimidin-5-yl-imino)methyl]naphthalen-2-ol

Conditions	Yield
In methanol at 63℃; for 0.5h; microwave irradiation;	86%

4,5-pyrimidinediamine (13754-19-3) + dimedone (126-81-8) → 3-(4-amino-pyrimidin-5-ylamino)-5,5-dimethyl-cyclohex-2-enone (1047619-57-7)

Conditions	Yield
In toluene Heating / reflux;	86%
In toluene Reflux;

4,5-pyrimidinediamine (13754-19-3) + 4-isothiocyanato-N-(quinoxalin-2-yl)benzenesulfonamide (681235-15-4) → 4-(9H-purin-8-ylamino)-N-(quinoxalin-2-yl)benzenesulfonamide

Conditions	Yield
With triethylamine In N,N-dimethyl-formamide for 8h; Reflux;	86%

4,5-pyrimidinediamine (13754-19-3) + pyrene-1-aldehyde (3029-19-4) → (pyren-1-ylmethylene)pyrimidine-2,4-diamine (1426931-11-4)

Conditions	Yield
In methanol for 12h; Reflux;	86%

4,5-pyrimidinediamine (13754-19-3) + Dimethyl N-(4-chloro-2-benzothiazolyl)-dithiocarbonimidate (83431-63-4) → (4-Chloro-benzothiazol-2-yl)-(9H-purin-8-yl)-amine (103588-21-2)

Conditions	Yield
In various solvent(s) Heating;	85%

4,5-pyrimidinediamine (13754-19-3) + 4-(4-methyl-5,5-dioxido-3-aphenylbenzo[e]pyrazolo[4,3-c][1,2]thiazin-2(4H)-yl)benzaldehyde (1608470-09-2) → 4-methyl-3-phenyl-2-[4-(9H-purin-8-yl)phenyl]-2,4-dihydropyrazolo[4,3c][1,2]benzothiazine 5,5-dioxide (1608470-27-4)

Conditions	Yield
Stage #1: 4-(4-methyl-5,5-dioxido-3-aphenylbenzo[e]pyrazolo[4,3-c][1,2]thiazin-2(4H)-yl)benzaldehyde With sodium metabisulfite In N,N-dimethyl-formamide at 20℃; Stage #2: 4,5-pyrimidinediamine In N,N-dimethyl-formamide	85%

4,5-pyrimidinediamine (13754-19-3) + C12H14N2S3 (103588-18-7) → (5,6-Dimethyl-benzothiazol-2-yl)-(9H-purin-8-yl)-amine (103588-22-3)

Conditions	Yield
In various solvent(s) Heating;	83%

4,5-pyrimidinediamine (13754-19-3) + (13C)-formic acid (1633-56-3) → C4(13)CH4N4

Conditions	Yield
In N,N-dimethyl acetamide at 120℃;	83%

4,5-pyrimidinediamine (13754-19-3) + 4-(3,4-dimethyl-5,5-dioxidobenzo[e]pyrazolo[4,3-c][1,2]-thiazin-2(4H)-yl)benzaldehyde (1350617-96-7) → 3,4-Dimethyl-2-[4-(9H-purin-8-yl)phenyl]-2,4-dihydropyrazolo[4,3-c][1,2] benzothiazine 5,5-dioxide (1608470-26-3)

Conditions	Yield
Stage #1: 4-(3,4-dimethyl-5,5-dioxidobenzo[e]pyrazolo[4,3-c][1,2]-thiazin-2(4H)-yl)benzaldehyde With sodium metabisulfite In N,N-dimethyl-formamide at 20℃; Stage #2: 4,5-pyrimidinediamine In N,N-dimethyl-formamide	83%

4,5-pyrimidinediamine (13754-19-3) + 4,6-Dimethylbicyclo<3.3.1>nona-3,6-diene-2,8-dione (31616-72-5) → C15H14N4 (82272-27-3)

Conditions	Yield
In acetic acid at 118℃; for 18h;	82%

4,5-pyrimidinediamine (13754-19-3) + C11H12N2OS3 (83431-64-5) → (6-Methoxy-benzothiazol-2-yl)-(9H-purin-8-yl)-amine (103588-20-1)

Conditions	Yield
In various solvent(s) Heating;	82%

4,5-pyrimidinediamine (13754-19-3) + ethyl 2-ethoxy-2-iminoacetate (816-27-3) → 6-amino-7-(8H)-pteridinone (1822-20-4)

Conditions	Yield
	80%
With potassium carbonate In ethanol for 2h; Heating;	80%

4,5-pyrimidinediamine (13754-19-3) + trifluoroacetic anhydride (407-25-0) → 8-(trifluoromethyl)-9H-purine (2268-12-4)

Conditions	Yield
In trifluoroacetic acid at 110℃; for 24h;	80%

4,5-pyrimidinediamine (13754-19-3) + methyl N-phenyldithiocarbamate (701-73-5) → C11H9N5 (103588-31-4)

Conditions	Yield
With potassium carbonate; copper(II) oxide In N,N-dimethyl-formamide at 60℃; for 1h;	80%

4,5-pyrimidinediamine (13754-19-3) + 4-methoxy-benzaldehyde (123-11-5) → 8-(4-methoxyphenyl)-7H-purine

Conditions	Yield
In neat (no solvent) at 200℃; for 6h;	80%

isonipecotic acid (498-94-2) + 4,5-pyrimidinediamine (13754-19-3) → 8-piperidin-4-yl-7H-purine

Conditions	Yield
With PPA at 100℃; for 2h;	78%

4,5-pyrimidinediamine (13754-19-3) + 1-acetyl-1H-indole-2,3-dione (574-17-4) → 7-(2-acetamidophenyl)-5H-pteridin-6-one (93065-32-8) + 6-(2-acetamidophenyl)-8H-pteridin-7-one (174320-65-1)

Conditions	Yield
In ethanol for 168h; Heating;	A 6% B 77%

4,5-pyrimidinediamine (13754-19-3) + C12H14NO6S(1-)*Na(1+) → morpholin-4-yl[4-(9h-purin-8-yl)phenyl]methanone

Conditions	Yield
In N,N-dimethyl-formamide at 120℃;	77%

4,5-pyrimidinediamine (13754-19-3) + 1,2-bis(3-bromophenyl)ethane-1,2-dione (91960-97-3) → C18H10Br2N4

Conditions	Yield
With acetic acid at 100℃; for 24h; Inert atmosphere;	75%

4,5-pyrimidinediamine (13754-19-3) → 5,8-dihydro-pteridine-6,7-dione (3947-46-4)

Conditions	Yield
With oxalic acid In hydrogenchloride	73%

4,5-pyrimidinediamine (13754-19-3) + sodium (4-fluorophenyl)(hydroxy)methanesulfonate → 8-(4-fluorophenyl)-9H-purine

Conditions	Yield
In N,N-dimethyl-formamide at 120℃;	72%

Upstream product

• 14631-08-4 2-chloro-4,5-diaminopyrimidine 
• 4316-98-7 6-chloro-4,5-diaminopyrimidine 
• 14623-58-6 4,5-diamino-1H-pyrimidine-2-thione 
• 1920-66-7 4-amino-2-chloro-5-nitropyrimidine 
• 16008-45-0 4-amino-5-formamidopyrimidine 
• 93135-56-9 (2R,3R,4R,5R)-2-(5-Amino-pyrimidin-4-ylamino)-tetrahydro-pyran-3,4,5-triol 
• 95103-63-2 9-(1-methoxyethyl)purine 
• 78105-09-6 9-(1-ethoxyethyl)-9H-purine 
• 95103-62-1 9-(1-Isopropoxy-ethyl)-9H-purine 
• 95103-65-4 9-[1-(2-Chloro-ethoxy)-ethyl]-9H-purine 
• 550-33-4 Nebularin 
• 10034-85-2 hydrogen iodide 

Downstream Products

• 120-73-0 purine 
• 16008-45-0 4-amino-5-formamidopyrimidine 
• 2432-26-0 5H-pteridin-6-one 
• 2432-27-1 8H-pteridin-7-one 
• 583-40-4 9H-purine-8(7H)-thione 
• 704-61-0 6,7-dimethyl-pteridine 
• 106582-53-0 6,7-diphenyl-pteridine 
• 13230-97-2 7H-purin-8(9H)-one 
• 936-40-3 7-methylpteridine 
• 273-40-5 8-Aza-7H-purin 
• 1128-60-5 7-methylpyrazino<2,3-d>pyrimidin-6(5H)-one 
• 16041-30-8 6-methylpyrazino<2,3-d>pyrimidin-7(8H)-one 
• 86475-08-3 2<(4-amino-5-pyrimidinyl)amine>-4-oxo-3-(hydroxymethyl)-4-phenyl-2-butenoic acid 
• 138196-65-3 4-aminopyrimidino-5-ammonium 4-benzoyl-2(5H)-furanone-3-oxide 

Relevant articles and documents

3-deoxyglucosone and skin

The invention relates to a method of removing 3-deoxyglucosone and other alpha-dicarbonyl sugars from skin. The invention further relates to methods of inhibiting production and function of 3-deoxyglucosone and other alpha-dicarbonyl sugars in skin. The invention also relates to methods of treating 3-deoxyglucosone and other alpha-dicarbonyl sugars associated diseases and disorders of skin.

Amino-substituted pyrimidines, derivatives and methods of use therefor

The present invention relates to compositions and methods for inhibiting nonenzymatic cross-linking (protein aging). Accordingly, a composition is disclosed which comprises an agent capable of inhibiting the formation of advanced glycosylation end products of target proteins by reacting with the carbonyl moiety of the early glycosylation product of such target proteins formed by their initial glycosylation. The method comprises contacting the target protein with the composition. Both industrial and therapeutic applications for the invention are envisioned, as food spoilage and animal protein aging can be treated.

Reaction of 9-(β-D-Ribofuranosyl)purine with Alkalies: Kinetics and Mechanism

The progress

Mechanisms for the Solvolytic Decomposition of Nucleoside Analogues. XI. Competitive Pathways for the Acidic Hydrolysis of 9-(β-D-Ribofuranosyl)purine

Kinetics and product distributions of the hydrolysis of 9-(β-D-ribofuranosyl)purine have been examined over a wide acidity range.At high oxonium ion concentrations rate-limiting departure of the mono- and diprotonated purinyl group with concomitant formation of a glycosyl oxocarbenium ion constitutes the major reaction pathway, analogous to the hydrolysis of 6-substituted purine nucleosides.In slightly acidic solutions opening of the imidazole ring of the base moiety prevails, and 4-amino-5-formamidopyrimidine, formed as a relatively stable intermediate, undergoes further hydrolysis to 4,5-diaminopyrimidine or cyclization to purine, the product composition depending on the acidity of the reaction solution.Rate constants for the partial reactions have been calculated and the mechanisms of the individual steps are discussed.

Mechanisms for the Solvolytic Decompositions of Nucleoside Analogues. IX. Pathways for the Alkyline Hydrolysis of 6-Substituted 9-(1-Ethoxyethyl)purines

A few 6-substituted 9-(1-ethoxyethyl)purines have been prepared and the rates of their base-catalyzed hydrolysis were measured by UV spectroscopy.The product mixtures were fractionated by preparative TLC and characterized by NMR and UV spectroscopy.The results obtained suggest that the alkaline cleavage of 9-(1-ethoxyethyl)purines generally proceeds by nucleophilic attack of hydroxide ion on C8 of the purine moiety, resulting in formation of appropriate 4,5-diaminopyrimidine and 8-methylpurine as final products.With 6-methoxy, 6-methylthio, and 6-chloro derivatives nucleophilic attack of hydroxide ion of C6 giving 9-(1-ethoxyethyl)hypoxanthine competes with this reaction.