5-Amino-4,6-dichloropyrimidine supplier

Name
5-Amino-4,6-dichloropyrimidine
EINECS 226-503-7
CAS No. 5413-85-4
Article Data31
CAS DataBase
Density 1.606 g/cm³
Solubility slightly soluble in water
Melting Point 145-148 °C(lit.)
Formula C₄H₃Cl₂N₃
Boiling Point 267.1 °C at 760 mmHg
Molecular Weight 163.994
Flash Point 115.3 °C
Transport Information
Appearance Yellowish-brown crystals or powder
Safety 26-36-24/25
Risk Codes 36/37/38
Molecular Structure
Hazard Symbols Xi
Synonyms 5-Pyrimidinamine, 4,6-dichloro-;4,6-Dichloro-5-aminopyrimidine;Pyrimidine, 5-amino-4,6-dichloro-;4,6-dichloropyrimidin-5-amine;4,6-Dichloropyrimidin-5-ylamine;
PSA 51.80000
LogP 1.94680

Synthetic route

: 4316-93-2
4,6-dichloro-5-nitropyrimidine

: 5413-85-4
5-amino-4,6-dichloropyridimine

Conditions

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

: 5413-85-4
5-amino-4,6-dichloropyridimine

Conditions

Conditions	Yield
	64%

: 69340-97-2
5-amino-4,6-dihydroxy-pyrimidine

: 5413-85-4
5-amino-4,6-dichloropyridimine

Conditions

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

: 64-18-6
formic acid

: 5413-85-4
5-amino-4,6-dichloropyridimine

: 123240-66-4
4,6-dichloro-5-formamidopyrimidine

Conditions

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%

: 5413-85-4
5-amino-4,6-dichloropyridimine

: 68-12-2, 33513-42-7
N,N-dimethyl-formamide

: N-(2-amino-4,6-dichloropyrimidin-5-yl)-N',N'-dimethylimidoformamide

Conditions

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

: 5413-85-4
5-amino-4,6-dichloropyridimine

: 138405-07-9
(+/-)-(1β,3α,4β)-3,4-bis(hydroxymethyl)-1-cyclobutylamine

: 138405-08-0
(+/-)-5-amino-4-chloro-6-<<(1β,3α,4β)-3,4-bis(hydroxymethyl)cyclopentan-1-yl>amino>pyrimidine

Conditions

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

: 5413-85-4
5-amino-4,6-dichloropyridimine

: 57260-71-6
1-t-Butoxycarbonylpiperazine

: 853679-43-3
tert-butyl 4-(5-amino-6-chloropyrimidin-4-yl)piperazine-1-carboxylate

Conditions

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

: 5413-85-4
5-amino-4,6-dichloropyridimine

: 63-74-1
sulfanilamide

: 4-((5-amino-6-chloropyrimidin-4-yl)amino)benzenesulfonamide

Conditions

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

: 5413-85-4
5-amino-4,6-dichloropyridimine

: 88474-32-2
4-chloro-5-cyano-1,2,3-triazole

Conditions

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

: 5413-85-4
5-amino-4,6-dichloropyridimine

: 106-47-8
4-chloro-aniline

: 103505-49-3
6-chloro-N4-(4-chlorophenyl)-4,5-pyrimidinediamine

Conditions

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%

: 5413-85-4
5-amino-4,6-dichloropyridimine

: 536-90-3
m-Anisidine

: 870257-99-1
6-chloro-N4-(3-methoxy-phenyl)-pyrimidine-4,5-diamine

Conditions

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

: 5413-85-4
5-amino-4,6-dichloropyridimine

: 556-61-6
methyl thioisocyanate

: 1-(7-chloro[1,3]thiazolo[5,4-d]pyrimidin-2-yl)-1,3-dimethylthiourea

Conditions

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

: 5413-85-4
5-amino-4,6-dichloropyridimine

: 637-89-8
4-sulfanylphenol

: 873106-32-2
5-amino-4,6-bis(p-hydroxyphenylthio)pyrimidine

Conditions

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

: 5413-85-4
5-amino-4,6-dichloropyridimine

: 98-80-6
phenylboronic acid

: 4,6-diphenylpyrimidin-5-amine

Conditions

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%

: 5413-85-4
5-amino-4,6-dichloropyridimine

: 4316-98-7
6-chloro-4,5-diaminopyrimidine

Conditions

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%

: 5413-85-4
5-amino-4,6-dichloropyridimine

: (+/-)-(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

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

: 5413-85-4
5-amino-4,6-dichloropyridimine

: 56777-11-8
4-chloro-<5-<14N>,6-<15N>>diaminopyrimidine

Conditions

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

: 5413-85-4
5-amino-4,6-dichloropyridimine

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

Conditions

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

: 5413-85-4
5-amino-4,6-dichloropyridimine

: C13H16N2O2

: C17H18ClN5O2

Conditions

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

: 107-10-8
propylamine

: 5413-85-4
5-amino-4,6-dichloropyridimine

: 195252-56-3
4,5-diamino-6-chloro-N4-propylpyrimidine

Conditions

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;

: 5413-85-4
5-amino-4,6-dichloropyridimine

: 103-72-0
phenyl isothiocyanate

: 871266-78-3
(7-chloro[1,3]thiazolo[5,4-d]pyrimidin-2-yl)(phenyl)amine

Conditions

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;

: 5413-85-4
5-amino-4,6-dichloropyridimine

: 106-54-7
p-Chlorothiophenol

: 873106-30-0
5-amino-4,6-bis(p-chlorophenylthio)pyrimidine

Conditions

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

: 5413-85-4
5-amino-4,6-dichloropyridimine

: 108-95-2
phenol

: 4-chloro-6-phenoxypyrimidin-5-amine

Conditions

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

: 5413-85-4
5-amino-4,6-dichloropyridimine

: 591-55-9
pyrimidin-5-amine

Conditions

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;

: 5413-85-4
5-amino-4,6-dichloropyridimine

: 91-00-9
Benzhydrylamine

: 5-Amino-4-(benzhydrylamino)-6-chloropyrimidine

Conditions

Conditions	Yield
	95%

: 5413-85-4
5-amino-4,6-dichloropyridimine

: 2,6-difluorobenzylamine hydrochloride

: 5-amino-4-chloro-6-<(2,6-difluorobenzyl)amino>pyrimidine

Conditions

Conditions	Yield
	95%

: 5413-85-4
5-amino-4,6-dichloropyridimine

: 64-04-0
phenethylamine

: 73840-54-7
6-chloro-N4-phenethylpyrimidine-4,5-diamine

Conditions

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%

: 5413-85-4
5-amino-4,6-dichloropyridimine

: 2284-20-0
4-Methoxyphenyl isothiocyanate

: (7-chloro[1,3]thiazolo[5,4-d]pyrimidin-2-yl)(4-methoxyphenyl)amine

Conditions

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%

: 5413-85-4
5-amino-4,6-dichloropyridimine

: 108-98-5
thiophenol

: 873106-27-5
5-amino-4,6-bis(phenylthio)pyrimidine

Conditions

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

: 5413-85-4
5-amino-4,6-dichloropyridimine

: 106-45-6
para-thiocresol

: 873106-29-7
5-amino-4,6-bis(p-tolylthio)pyrimidine

Conditions

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

: 5413-85-4
5-amino-4,6-dichloropyridimine

: 122-97-4
3-Phenyl-1-propanol

: 4-chloro-6-(3-phenylpropoxy)pyrimidin-5-amine

Conditions

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%

: 5413-85-4
5-amino-4,6-dichloropyridimine

: 64-17-5
ethanol

: 55150-17-9
4-ethoxypyrimidin-5-amine

Conditions

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

5-Amino-4,6-dichloropyrimidine Specification

The IUPAC name of 5-Amino-4,6-dichloropyrimidine is 4,6-dichloropyrimidin-5-amine. With the CAS registry number 5413-85-4 and EINECS 226-503-7, it is also named as 5-Pyrimidinamine, 4,6-dichloro-. The product's categories are Pyridines, Pyrimidines, Purines and Pteredines; Pyrimidines; Heterocyclic Compounds; Bases & Related Reagents; Heterocycles; Nucleotides; Building Blocks; Heterocyclic Building Blocks. It is yellowish-brown crystals or powder which is stable under normal temperature and pressure. Additionally, this chemical should be sealed in the container, kept away from direct sunshine and stored in the cool and dry place.

The other characteristics of this product can be summarized as: (1)ACD/LogP: 0.76; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 0.76; (4)ACD/LogD (pH 7.4): 0.76; (5)ACD/BCF (pH 5.5): 2.23; (6)ACD/BCF (pH 7.4): 2.23; (7)ACD/KOC (pH 5.5): 61.73; (8)ACD/KOC (pH 7.4): 61.73; (9)#H bond acceptors: 3; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 1; (12)Polar Surface Area: 29.02 Å²; (13)Index of Refraction: 1.633; (14)Molar Refractivity: 36.46 cm³; (15)Molar Volume: 102 cm³; (16)Polarizability: 14.45×10^-24 cm³; (17)Surface Tension: 68 dyne/cm; (18)Density: 1.606 g/cm³; (19)Flash Point: 115.3 °C; (20)Enthalpy of Vaporization: 50.51 kJ/mol; (21)Boiling Point: 267.1 °C at 760 mmHg; (22)Vapour Pressure: 0.00832 mmHg at 25°C.

Preparation of 5-Amino-4,6-dichloropyrimidine: It can be obtained by 4,6-dichloro-5-nitro-pyrimidine. This reaction needs reagent SnCl₂*2H₂O and solvent ethanol by heating. The reaction time is 20 min. The yield is 91%.

Uses of 5-Amino-4,6-dichloropyrimidine: It is an intermediate in the production of many biological inhibitors. And it can react with furfurylamine to get 6-chloro-N⁴-furfuryl-pyrimidine-4,5-diyldiamine. This reaction needs reagent triethylamine and solvent butan-1-ol at ambient temperature. The reaction time is 2 hours. The yield is 78%.

5-Amino-4,6-dichloropyrimidine can react with furfurylamine to get 6-chloro-N4-furfuryl-pyrimidine-4,5-diyldiamine

When you are using this chemical, please be cautious about it as the following:
It is irritating to eyes, respiratory system and skin. So people should avoid contact with skin and eyes. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. If you want to contact this product, you must wear suitable protective clothing.

People can use the following data to convert to the molecule structure.
1. SMILES:Clc1ncnc(Cl)c1N
2. InChI:InChI=1/C4H3Cl2N3/c5-3-2(7)4(6)9-1-8-3/h1H,7H2
3. InChIKey:NIGDWBHWHVHOAD-UHFFFAOYAN

Product Name

5-Amino-4,6-dichloropyrimidine

Synthetic route

5-Amino-4,6-dichloropyrimidine Specification

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