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
• Article Data: 6

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

Chemical Properties

Brown crystals

Uses

4,5-Diaminopyrimidine is an intermediate in the synthesis of Nisin, a compound that was first introduced as a good preservative and was later on discovered to have antibacterial activity against gram positive bacteria. 4,5-Diaminopyrimidine is also used as a reagent to synthesize uracil-based 2-aminoanilide derivatives, compounds that act as histone deacetylase inhibitors.

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

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

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.

Mechanisms for the solvolytic decompositions of nucleoside analogues. XII. Further studies on the alkaline hydrolysis of 9-(1-alkoxyethyl)purines

-

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

The progress