156-83-2

Basic information

• Product Name: 4-Chloro-2,6-diaminopyrimidine
• Synonyms: 4-DiaMino-6-chloropyriMidine;NSC 8818;DIAMINO-6-CHLOROPYRIMIDINE, 2,4-(SH);2,4-DIAMINO-6-CHLOROPYRIMIDINE FOR SYNTH;4-Chloro-2,6-diaminopyrimidine, 4-Chloro-2,6-diamino-1,3-diazine;2,6-DiaMino-4-chloropyriMidine 98%;DiaMino-6-chloropyriMid;2,4-Diamino-6-chloropyrimidine,98%
• CAS NO: 156-83-2
• Molecular Formula: C₄H₅ClN₄
• Molecular Weight: 144.5623
• EINECS: 205-863-9
• Product Categories: Heterocycle-Pyrimidine series;PYRIMIDINE;Pyridines, Pyrimidines, Purines and Pteredines;Heterocyclic Compounds;Pyrimidines;Bases & Related Reagents;Heterocycles;Nucleotides
• Mol File: 156-83-2.mol
• Article Data: 9

Chemical Properties

• Melting Point: 199-202 °C(lit.)
• Boiling Point: 199-202 °C
• Flash Point: 218.9 °C
• Appearance: white cyrstalline solid
• Density: 1.3966 (rough estimate)
• Vapor Pressure: 7.01E-08mmHg at 25°C
• Refractive Index: 1.6010 (estimate)
• Storage Temp.: -20°C Freezer
• Solubility: slightly soluble
• PKA: 3.66±0.10(Predicted)
• Water Solubility: slightly soluble
• BRN: 118455
• CAS DataBase Reference: 4-Chloro-2,6-diaminopyrimidine(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Chloro-2,6-diaminopyrimidine(156-83-2)
• EPA Substance Registry System: 4-Chloro-2,6-diaminopyrimidine(156-83-2)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 22-36/37/38
• Safety Statements: 26-24/25
• WGK Germany: 3
• Hazardous Substances Data: 156-83-2(Hazardous Substances Data)

Usage

Chemical Properties

White Cyrstalline Solid

Uses

Melamine and Related Compounds in Dog Food Using GC-MS

Purification Methods

It recrystallises from boiling H2O (charcoal) as needles; it also crystallises from Me2CO. [Büttner Chem Ber 36 2232 1903, Roth J Am Chem Soc 72 1914 1950, UV: Brown & Jacobsen J Chem Soc 3172 1962, Beilstein 24 H 318, 25 III/IV 2788.]

InChI:InChI=1/C4H5ClN4/c5-2-1-3(6)9-4(7)8-2/h1H,(H4,6,7,8,9)

Synthetic route

2,6-diaminopyrimidin-4-ol (56-06-4) → 6-chloro-pyrimidine-2,4-diyldiamine (156-83-2)

Conditions	Yield
With trichlorophosphate at 97℃; for 17h;	85%
With trichlorophosphate for 3h; Reflux;	73%

hypochloric acid (14989-30-1) + 2,6-diaminopyrimidin-4-ol (56-06-4) → 6-chloro-pyrimidine-2,4-diyldiamine (156-83-2)

Conditions	Yield
With sodium hydroxide; potassium carbonate; trichlorophosphate In tetrahydrofuran; water; acetone	47.3%

2,4-diamino-6-chloropyrimidine hydrochloride → 6-chloro-pyrimidine-2,4-diyldiamine (156-83-2)

Conditions	Yield
With pyrographite In water at 70℃;

2-amino-4-chloro-6-guanidinopyrimidine (83170-03-0) → 6-chloro-pyrimidine-2,4-diyldiamine (156-83-2)

Conditions	Yield
With ammonia In ethanol at 190℃;

2,6-diamino-3H-pyrimidin-4-one (100643-27-4, 143504-99-8) → 6-chloro-pyrimidine-2,4-diyldiamine (156-83-2)

Conditions	Yield
With trichlorophosphate

4-amino-2,6-dichloropyrimidine (10132-07-7) → 6-chloro-pyrimidine-2,4-diyldiamine (156-83-2)

Conditions	Yield
With ethanol; ammonia at 160℃;

2-Amino-4,6-dichloropyrimidine (56-05-3) → 6-chloro-pyrimidine-2,4-diyldiamine (156-83-2)

Conditions	Yield
With ethanol; ammonia at 160℃;

2,4,6-trichloropyrimidine (3764-01-0) → 2,4,6-triaminopyrimidine (1004-38-2) + 6-chloro-pyrimidine-2,4-diyldiamine (156-83-2)

Conditions	Yield
With ethanol; ammonia at 160℃;

2,4,6-trichloropyrimidine (3764-01-0) + ammonia (7664-41-7) → 6-chloro-pyrimidine-2,4-diyldiamine (156-83-2)

Conditions	Yield
at 160℃;

4-amino-2,6-dichloropyrimidine (10132-07-7) + ammonia (7664-41-7) → 6-chloro-pyrimidine-2,4-diyldiamine (156-83-2)

Conditions	Yield
at 160℃;

2-Amino-4,6-dichloropyrimidine (56-05-3) + ammonia (7664-41-7) → 6-chloro-pyrimidine-2,4-diyldiamine (156-83-2)

Conditions	Yield
at 160℃;

Upstream product

• 3764-01-0 2,4,6-trichloropyrimidine 
• 10132-07-7 4-amino-2,6-dichloropyrimidine 
• 14989-30-1 hypochloric acid 
• 56-06-4 2,6-diaminopyrimidin-4-ol 
• 71340-69-7 2,4-diamino-6-chloropyrimidine hydrochloride 
• 56-05-3 2-Amino-4,6-dichloropyrimidine 
• 7664-41-7 ammonia 
• 83170-03-0 2-amino-4-chloro-6-guanidinopyrimidine 
• 100643-27-4 2,6-diamino-3H-pyrimidin-4-one 

Downstream Products

• 24867-26-3 2,4-Diamino-6-piperidinopyrimidine 
• 3270-97-1 2,4-diamino-6-methoxypyrimidine 
• 116436-03-4 6-ethoxypyrimidine-2,4-diamine 
• 34388-37-9 N⁴-(4-arsenoso-phenyl)-pyrimidine-2,4,6-triyltriamine 
• 857428-91-2 6-butoxy-pyrimidine-2,4-diyldiamine 
• 49753-53-9 N⁴-p-tolyl-pyrimidine-2,4,6-triamine 
• 64414-74-0 N⁴-(4-chlorophenyl)pyrimidine-2,4,6-triamine 
• 24867-25-2 N⁴,N⁴-dimethyl-2,4,6-pyrimidinetriamine 
• 859064-95-2 2,4-Diamino-6-(2-diethylamino-ethylamino)-pyrimidin 
• 17419-08-8 N⁴-phenyl-pyrimidine-2,4,6-triamine 
• 100139-23-9 N⁴-benzyl-N⁴-methyl-pyrimidine-2,4,6-triyltriamine 
• 24867-24-1 6-chloro-2,4-diaminopyrimidine 
• 156-81-0 2,4-diaminopyrimidine 
• 727651-44-7 2,4-diamino-6-iodopyrimidine 

Relevant articles and documents

Synthesis and anticancer activity of some pyrimidine derivatives with aryl urea moieties as apoptosis-inducing agents

A new series of pyrimidine derivatives containing aryl urea moieties was designed and synthesized. The anticancer activities of all compounds were evaluated in vitro against colon and prostat cancer cell lines by MTT assay. Among these compounds, 4b exhibited the highest cytotoxic activity against SW480 cancer cell line with IC50 value of 11.08 μM. Mechanistic studies showed that compound 4b arrested cell cycle at G2/M phase and induced apoptosis through upregulating Bax, Ikb-α and cleaved PARP and downregulating Bcl-2 expression levels. Moreover, compound 4b induced loss of mitochondrial membrane potential in SW480 cells. These results suggest that pyrimidine with urea moieties could be a template for designing new anticancer agents.

Method for synthesizing 2,4-diamino-6-chloropyrimidine

The invention discloses a method for synthesizing 2,4-diamino-6-chloropyrimidine. According to the method, methyl cyanoacetate, guanidine nitrate and sodium methoxide serve as raw materials to react with one another to obtain 2,4-diamino-6-hydroxypyrimidine, and then 2,4-diamino-6-hydroxypyrimidine is chloridized with POCl3 in the presence of triethylamine to obtain 2,4-diamino-6-chloropyrimidine.Compared with the prior art, the situation that the whole reactant is neutralized to generate and precipitate a large amount of phosphate is avoided, the product purity is improved, the product yieldis increased, the situation that a solvent is used for refining DACP is avoided, the process is greatly simplified, the cost is reduced, the yield is increased, and the method has the advantages of being high in yield, easy to operate and high in safety and is a very effective process suitable for industrialized mass production.

ARYL PYRIMIDINE DERIVATIVES

The aryl pyrimidine derivatives and pharmaceutically acceptable salts and N-oxides thereof, exhibit useful pharmacological properties, including utility as selective 5HT 2B-antagonists.