5413-85-4

Basic information

• Product Name: 5-Amino-4,6-dichloropyrimidine
• Synonyms: 4,6-DICHLORO-5-PYRIMIDINAMINE;4,6-DICHLOROPYRIMIDIN-5-AMINE;4,6-DICHLOROPYRIMIDIN-5-YLAMINE;5-AMINO-4,6-DICHLOROPYFIMIDINE;5-AMINO-4,6-DICHLOROPYRIMIDINE;AKOS 91433;5-PYRIMIDINAMINE, 4,6-DICHLORO-;4,6-Dichloro-5-aminopyrimidine
• CAS NO: 5413-85-4
• Molecular Formula: C₄H₃Cl₂N₃
• Molecular Weight: 163.99
• EINECS: 226-503-7
• Product Categories: Pyridines, Pyrimidines, Purines and Pteredines;Pyrimidine;Pyrimidines;Heterocyclic Compounds;Bases & Related Reagents;Heterocycles;Nucleotides;Building Blocks;Halogenated Heterocycles;Heterocyclic Building Blocks;PyrimidinesHeterocyclic Building Blocks;Aromatics;Heterocycle-Pyrimidine series
• Mol File: 5413-85-4.mol
• Article Data: 21

Chemical Properties

• Melting Point: 145-148 °C(lit.)
• Boiling Point: 270.44°C (rough estimate)
• Flash Point: 115.3 °C
• Appearance: Yellow-brown/Crystals or Powder
• Density: 1.6662 (rough estimate)
• Vapor Pressure: 0.00832mmHg at 25°C
• Refractive Index: 1.6300 (estimate)
• Storage Temp.: 2-8°C
• Solubility: slightly soluble
• PKA: -3.01±0.26(Predicted)
• Water Solubility: slightly soluble
• Sensitive: Moisture Sensitive
• BRN: 126885
• CAS DataBase Reference: 5-Amino-4,6-dichloropyrimidine(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Amino-4,6-dichloropyrimidine(5413-85-4)
• EPA Substance Registry System: 5-Amino-4,6-dichloropyrimidine(5413-85-4)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-24/25
• WGK Germany: 3
• F: 10-21
• TSCA: Yes
• Hazardous Substances Data: 5413-85-4(Hazardous Substances Data)

Usage

Chemical Properties

Yellowish-brown crystals or powder

Uses

Different sources of media describe the Uses of 5413-85-4 differently. You can refer to the following data:
1. An intermediate in the production of many biological inhibitors.
2. 5-Amino-4,6-dichloropyrimidine was used in the synthesis of:oxepane ring containing monocyclic, conformationally restricted bicyclic and spirocyclic nucleosidesconformationally locked bicyclo[2.2.1]heptane/oxa-bicyclo[3.2.1]octane nucleosidesN(7)-substituted purineschiral derivatives of (+)-erythro-9-(2-hydroxy-3-nonyl)adenine9-alkyl-6-substituted-purine analogs, potent anticonvulsant agentspyrimido-oxazepines in a three-step process with microwave heating at 150°C

InChI:InChI=1/C4H3Cl2N3/c5-3-2(7)4(6)9-1-8-3/h1H,7H2

Synthetic route

4,6-dichloro-5-nitropyrimidine (4316-93-2) → 5-amino-4,6-dichloropyridimine (5413-85-4)

Conditions	Yield
With tin(ll) chloride In ethanol for 1h; Heating;	99%
With tin(ll) chloride In ethanol for 0.333333h; Heating;	91%
With palladium 10% on activated carbon; hydrogen In ethyl acetate at 20℃; for 4h;	86%

7-((3aR,4R,6R,6aR)-6-(((tert-butyldimethylsilyl)oxy)methyl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine → 5-amino-4,6-dichloropyridimine (5413-85-4)

Conditions	Yield
	64%

5-amino-4,6-dihydroxy-pyrimidine (69340-97-2) → 5-amino-4,6-dichloropyridimine (5413-85-4)

Conditions	Yield
With tetraethylammonium chloride; trichlorophosphate at 80 - 110℃; for 3h;	54.1%
With trichlorophosphate at 110℃; for 48h; Inert atmosphere; Sealed tube;	44 mg
With trichlorophosphate at 110℃; for 48h; Sealed tube; Inert atmosphere;	44 mg

formic acid (64-18-6) + 5-amino-4,6-dichloropyridimine (5413-85-4) → 4,6-dichloro-5-formamidopyrimidine (123240-66-4)

Conditions	Yield
With acetic anhydride at 20℃; for 2h;	100%
With acetic anhydride at 0 - 20℃; for 2.5h;	100%
With acetic acid at 0 - 30℃; Autoclave; Large scale;	89.7%

5-amino-4,6-dichloropyridimine (5413-85-4) + N,N-dimethyl-formamide (68-12-2, 33513-42-7) → N-(2-amino-4,6-dichloropyrimidin-5-yl)-N',N'-dimethylimidoformamide

Conditions	Yield
With thionyl chloride at 0 - 20℃; for 1h; Inert atmosphere;	100%

5-amino-4,6-dichloropyridimine (5413-85-4) + (+/-)-(1β,3α,4β)-3,4-bis(hydroxymethyl)-1-cyclobutylamine (138405-07-9) → (+/-)-5-amino-4-chloro-6-<<(1β,3α,4β)-3,4-bis(hydroxymethyl)cyclopentan-1-yl>amino>pyrimidine (138405-08-0)

Conditions	Yield
With triethylamine In butan-1-ol for 48h; Heating;	99%
With triethylamine In butan-1-ol at 100℃; for 48h;	48%

5-amino-4,6-dichloropyridimine (5413-85-4) + 1-t-Butoxycarbonylpiperazine (57260-71-6) → tert-butyl 4-(5-amino-6-chloropyrimidin-4-yl)piperazine-1-carboxylate (853679-43-3)

Conditions	Yield
In triethylamine; toluene for 12h; Heating / reflux;	99%

5-amino-4,6-dichloropyridimine (5413-85-4) + sulfanilamide (63-74-1) → 4-((5-amino-6-chloropyrimidin-4-yl)amino)benzenesulfonamide

Conditions	Yield
With toluene-4-sulfonic acid In 1,4-dioxane; water Reflux;	99%

5-amino-4,6-dichloropyridimine (5413-85-4) → 4-chloro-5-cyano-1,2,3-triazole (88474-32-2)

Conditions	Yield
With hydrogenchloride; sodium nitrite In water 1.)-5 deg C, 1.5 h 2.)20 deg C, 1.5 h;	98%

5-amino-4,6-dichloropyridimine (5413-85-4) + 4-chloro-aniline (106-47-8) → 6-chloro-N4-(4-chlorophenyl)-4,5-pyrimidinediamine (103505-49-3)

Conditions	Yield
With hydrogenchloride In ethanol; water at 20 - 82℃; for 79h;	98%
With hydrogenchloride In ethanol; water at 20 - 82℃; for 79h;	98%
With hydrogenchloride In ethanol; water at 20 - 82℃; for 79h;	98%

5-amino-4,6-dichloropyridimine (5413-85-4) + m-Anisidine (536-90-3) → 6-chloro-N4-(3-methoxy-phenyl)-pyrimidine-4,5-diamine (870257-99-1)

Conditions	Yield
In ethanol	98%
In ethanol at 80℃; Acidic conditions;	80%
With hydrogenchloride In ethanol; water for 24h; Heating;	68%

5-amino-4,6-dichloropyridimine (5413-85-4) + methyl thioisocyanate (556-61-6) → 1-(7-chloro[1,3]thiazolo[5,4-d]pyrimidin-2-yl)-1,3-dimethylthiourea

Conditions	Yield
With caesium carbonate In acetonitrile at 50℃; for 16h;	98%

5-amino-4,6-dichloropyridimine (5413-85-4) + 4-sulfanylphenol (637-89-8) → 5-amino-4,6-bis(p-hydroxyphenylthio)pyrimidine (873106-32-2)

Conditions	Yield
With triethylamine In butan-1-ol Heating;	98%

5-amino-4,6-dichloropyridimine (5413-85-4) + phenylboronic acid (98-80-6) → 4,6-diphenylpyrimidin-5-amine

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In ethanol; water; toluene Suzuki-Miyaura Coupling; Reflux;	98%
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In ethanol; water; toluene for 20h; Inert atmosphere; Reflux;	98%
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane; water at 80℃; for 16h; Suzuki-Miyaura Coupling; Inert atmosphere; regioselective reaction;	91%

5-amino-4,6-dichloropyridimine (5413-85-4) → 6-chloro-4,5-diaminopyrimidine (4316-98-7)

Conditions	Yield
With ammonia In water at 100℃; for 46h;	97%
With ammonia at 100℃; for 46h;	97%
With ammonia In water at 100℃; for 46h;	97%

5-amino-4,6-dichloropyridimine (5413-85-4) + (+/-)-(1α,2β,3α,4α)-4-amino-2-fluoro-3-hydroxycyclopentanemethanol → (1S,2S,3S,5S)-5-(5-Amino-6-chloro-pyrimidin-4-ylamino)-2-fluoro-3-hydroxymethyl-cyclopentanol

Conditions	Yield
With triethylamine In butan-1-ol at 120℃; for 48h;	97%

5-amino-4,6-dichloropyridimine (5413-85-4) → 4-chloro-<5-<14N>,6-<15N>>diaminopyrimidine (56777-11-8)

Conditions	Yield
With ammonia In ethanol at 120 - 130℃; under 5171.5 Torr; for 7h;	97%
With ammonia at 120 - 140℃; under 5171.5 Torr; for 7h;	95%
With [15N]ammonia In ethanol at 140℃; for 4h;	81%
With (15N)-ammonium chloride; potassium hydrogencarbonate In dimethyl sulfoxide at 80℃; for 50h;	4.3 mmol

(+/-)-(1R,4R,7S)-7-aminobicyclo[2.2.1]hept-5-ene-2,2-dimethanol + 5-amino-4,6-dichloropyridimine (5413-85-4) → (+/-)-(1R,4R,7S)-7-[(5-amino-6-chloropyrimidin-4-yl)amino]bicyclo[2.2.1]hept-5-ene-2,2-dimethanol

Conditions	Yield
With triethylamine In ethanol at 105℃; for 144h;	97%

5-amino-4,6-dichloropyridimine (5413-85-4) + C13H16N2O2 → C17H18ClN5O2

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In butan-1-ol at 117℃; for 48h;	97%

propylamine (107-10-8) + 5-amino-4,6-dichloropyridimine (5413-85-4) → 4,5-diamino-6-chloro-N4-propylpyrimidine (195252-56-3)

Conditions	Yield
With triethylamine In ethanol at 80℃; for 8h;	96%
With triethylamine In butan-1-ol for 16h; Heating;	95%
In water; isopropyl alcohol at 80℃; for 16h;
With N-ethyl-N,N-diisopropylamine In 1,4-dioxane at 100℃; for 16h;

5-amino-4,6-dichloropyridimine (5413-85-4) + phenyl isothiocyanate (103-72-0) → (7-chloro[1,3]thiazolo[5,4-d]pyrimidin-2-yl)(phenyl)amine (871266-78-3)

Conditions	Yield
With potassium fluoride on basic alumina In acetonitrile at 60℃; for 5h; Reagent/catalyst; Solvent; Temperature; Time;	96%
In acetonitrile at 60℃; for 5h;	96%
With caesium carbonate In acetonitrile at 50℃; for 16h;	92%
With caesium carbonate In acetonitrile at 50℃; for 12h;

5-amino-4,6-dichloropyridimine (5413-85-4) + p-Chlorothiophenol (106-54-7) → 5-amino-4,6-bis(p-chlorophenylthio)pyrimidine (873106-30-0)

Conditions	Yield
With triethylamine In butan-1-ol Heating;	96%

5-amino-4,6-dichloropyridimine (5413-85-4) + phenol (108-95-2) → 4-chloro-6-phenoxypyrimidin-5-amine

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 60℃; for 18h;	96%

5-amino-4,6-dichloropyridimine (5413-85-4) → pyrimidin-5-amine (591-55-9)

Conditions	Yield
With sodium hydroxide; hydrogen; palladium on activated charcoal In diethyl ether at 25℃; under 1551.44 Torr;	95%
With sodium hydroxide; hydrogen; palladium 10% on activated carbon In diethyl ether; water at 20℃; for 72h;	31.9%
With palladium on activated charcoal Hydrogenation;

5-amino-4,6-dichloropyridimine (5413-85-4) + Benzhydrylamine (91-00-9) → 5-Amino-4-(benzhydrylamino)-6-chloropyrimidine

Conditions	Yield
	95%

5-amino-4,6-dichloropyridimine (5413-85-4) + 2,6-difluorobenzylamine hydrochloride → 5-amino-4-chloro-6-<(2,6-difluorobenzyl)amino>pyrimidine

Conditions	Yield
	95%

5-amino-4,6-dichloropyridimine (5413-85-4) + phenethylamine (64-04-0) → 6-chloro-N4-phenethylpyrimidine-4,5-diamine (73840-54-7)

Conditions	Yield
With triethylamine In butan-1-ol at 100℃; for 12h;	95%
With triethylamine In butan-1-ol for 5h; Inert atmosphere; Schlenk technique;	92%
With triethylamine In butan-1-ol at 120℃; for 4h; Heating / reflux;	90%

5-amino-4,6-dichloropyridimine (5413-85-4) + 4-Methoxyphenyl isothiocyanate (2284-20-0) → (7-chloro[1,3]thiazolo[5,4-d]pyrimidin-2-yl)(4-methoxyphenyl)amine

Conditions	Yield
With caesium carbonate In acetonitrile at 50℃; for 16h;	95%
With potassium fluoride on basic alumina In acetonitrile at 60℃; for 5h;	91%
In acetonitrile at 60℃; for 5h;	91%

5-amino-4,6-dichloropyridimine (5413-85-4) + thiophenol (108-98-5) → 5-amino-4,6-bis(phenylthio)pyrimidine (873106-27-5)

Conditions	Yield
With triethylamine In butan-1-ol Heating;	95%
With triethylamine In butan-1-ol Heating / reflux;	95%

5-amino-4,6-dichloropyridimine (5413-85-4) + para-thiocresol (106-45-6) → 5-amino-4,6-bis(p-tolylthio)pyrimidine (873106-29-7)

Conditions	Yield
With triethylamine In butan-1-ol Heating;	95%

5-amino-4,6-dichloropyridimine (5413-85-4) + 3-Phenyl-1-propanol (122-97-4) → 4-chloro-6-(3-phenylpropoxy)pyrimidin-5-amine

Conditions	Yield
Stage #1: 3-Phenyl-1-propanol With sodium hydride In tetrahydrofuran at 20℃; for 0.666667h; Inert atmosphere; Stage #2: 5-amino-4,6-dichloropyridimine In tetrahydrofuran at 0 - 20℃; Inert atmosphere;	95%

5-amino-4,6-dichloropyridimine (5413-85-4) + ethanol (64-17-5) → 4-ethoxypyrimidin-5-amine (55150-17-9)

Conditions	Yield
With sodium hydroxide; hydrogen; palladium 10% on activated carbon In tetrahydrofuran at 20℃; for 24h;	94.3%

Upstream product

• 69340-97-2 5-amino-4,6-dihydroxy-pyrimidine 
• 4316-93-2 4,6-dichloro-5-nitropyrimidine 

Downstream Products

• 98140-03-5 6-chloro-N⁴-ethylpyrimidine-4,5-diamine 
• 41259-65-8 6-chloro-N₄-phenylpyrimidine-4,5-diamine 
• 52602-68-3 6-chloro-N⁴-methylpyrimidine-4,5-diamine 
• 591-55-9 pyrimidin-5-amine 
• 54851-35-3 5-amino-6-chloro-3H-pyrimidine-4-thione 
• 4316-98-7 6-chloro-4,5-diaminopyrimidine 
• 13190-82-4 (+/-)-(1RS,2SR,3RS,5RS)-3-(5-amino-6-chloro-pyrimidin-4-yl-amino)-5-hydroxymethyl-cyclopentane-1,2-diol 
• 17435-30-2 (R)-1-(5-Amino-6-chloro-pyrimidin-4-ylamino)-propan-2-ol 
• 195252-56-3 4,5-diamino-6-chloro-N⁴-propylpyrimidine 
• 195252-58-5 N⁴-sec-Butyl-6-chloro-pyrimidine-4,5-diamine 
• 195252-59-6 6-Chloro-N⁴-isobutyl-pyrimidine-4,5-diamine 
• 5449-10-5 6-chloro-N⁴-cyclohexyl-pyrimidine-4,5-diamine 
• 18202-82-9 4-isopropylamino-5-amino-6-chloropyrimidine 
• 41259-67-0 N⁴-butyl-6-chloropyrimidine-4,5-diamine 

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