ChemicalBook Product Catalog Pharmaceutical intermediates Heterocyclic compound Pyrimidines Chloropyrimidine 2,4-Dichloropyrimidine

2,4-Dichloropyrimidine

Product Name2,4-Dichloropyrimidine
CAS3934-20-1
MFC4H2Cl2N2
MW148.98
EINECS223-508-6
MOL File3934-20-1.mol

Chemical Properties

Melting point	57-61 °C (lit.)
Boiling point	101 °C/23 mmHg (lit.)
Density	1.6445 (rough estimate)
refractive index	1.6300 (estimate)
Flash point	101°C/23mm
storage temp.	Keep in dark place,Sealed in dry,Room Temperature
solubility	Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly)
pka	-2.84±0.20(Predicted)
form	Powder, Crystals and/or Chunks
color	White to yellow to beige or grayish
Water Solubility	Soluble in water (partly), methanol, chloroform, and ethyl acetate.
Sensitive	Moisture Sensitive
BRN	110911
InChI	1S/C4H2Cl2N2/c5-3-1-2-7-4(6)8-3/h1-2H
InChIKey	BTTNYQZNBZNDOR-UHFFFAOYSA-N
SMILES	Clc1ccnc(Cl)n1
CAS DataBase Reference	3934-20-1(CAS DataBase Reference)
NIST Chemistry Reference	Pyrimidine, 2,4-dichloro-(3934-20-1)
EPA Substance Registry System	Pyrimidine, 2,4-dichloro- (3934-20-1)

Safety Information

Hazard Codes	Xi
Risk Statements	36/37/38
Safety Statements	26-36-28A
RIDADR	1759
WGK Germany	3
TSCA	TSCA listed
HazardClass	8
PackingGroup	III
HS Code	29335990
Storage Class	11 - Combustible Solids
Hazard Classifications	Eye Irrit. 2 Skin Irrit. 2 STOT SE 3

MSDS

Provider	Language
2,4-Dichloropyrimidine	English
SigmaAldrich	English
ACROS	English
ALFA	English

Usage And Synthesis

Chemical Properties

White Solid

Uses

2,4-Dichloropyrimidine was used in the synthesis of medicinally important 4-aryl-5-pyrimidinylimidazoles.

Preparation

Obtained by chlorination of uracil. Add uracil, phosphorus trichloride, and xylene amine into the reaction pot, heat to 130 ℃, reflux for about 45min, slightly cool, put in crushed ice, that is, the precipitation of purple solid, filtered while hot and not dissolved, washed with ice water, vacuum drying, a kind of purple crude, decolorized with petroleum ether (boiling range of 60-90 ℃), recrystallized, obtained 2,4-dichloropyrimidine.

General Description

2,4-Dichloropyrimidine is a human skin sensitizer. It undergoes effective one-pot, regioselective double Suzuki coupling reaction to yield diarylated pyrimidines.

Reactivity Profile

The reaction of N-substituted cyclic amines with 2,4-dichloroquinazoline and 2,4-dichloro-5-methyl-pyrimidine afforded 2-amino-4-chloroquinazolines and 2-amino-4-chloro-5-methylpyrimidines, respectively—the reaction of these amines with 2,4-dichloropyrimidine 3a afforded not only 2-amino-4-chloropyrimidines but also the isomeric 4-amino-2-chloropyrimidines. An effective one-pot, regioselective double Suzuki coupling of 2,4-dichloropyrimidine has been developed. This method enables the quick and efficient synthesis of diarylated pyrimidines. The choice of solvent proved critical to the success of this reaction sequence, with alcoholic solvent mixtures affording much greater reactivity and correspondingly lower temperatures than polar aprotic solvents[5-6].

Synthesis

66-22-8

3934-20-1

The general procedure for the synthesis of 2,4-dichloropyrimidine from pyrimidine-2,4(1H,3H)-dione is as follows: in a 500 mL two-necked round-bottomed flask equipped with a condenser tube, pyrimidine-2,4(1H,3H)-dione (100 g, 0.82 mol) was dissolved in phosphoryl chloride (400 mL). The reaction mixture was refluxed with stirring at 110°C for 3.5 hours. Upon completion of the reaction, unreacted phosphoryl chloride was removed by distillation at 50°C under reduced pressure. The reaction was quenched by slowly pouring the residue into 50 g of ice, followed by extraction with chloroform (3 x 50 mL). The organic phases were combined, washed with dilute sodium carbonate solution and dried with anhydrous sodium sulfate. Finally, the solvent was removed by distillation under reduced pressure to give the target product 2,4-dichloropyrimidine.

References

[1] DR. AGNES FIZIA. Cyclopalladation in the Periphery of a NHC Ligand as the Crucial Step in the Synthesis of Highly Active Suzuki–Miyaura Cross-Coupling Catalysts[J]. Chemistry - A European Journal, 2017. DOI:10.1002/chem.201702877.
[2] FABIAN BRUENING Lucie E L. Highly Regioselective Organocatalytic SNAr Amination of 2,4-Dichloropyrimidine and Related Heteroaryl Chlorides[J]. European Journal of Organic Chemistry, 2017. DOI:10.1002/ejoc.201700459.
[3] ANDERSONSAMANTHA C HandyScott T. One-pot Double Suzuki Couplings of Dichloropyrimidines.[J]. Synthesis-Stuttgart, 2010. DOI:10.1055/s-0030-1258150.
[4] TOMá KUBELKA. Synthesis of 2,4-Disubstituted Pyrimidin-5-yl C-2′-Deoxyribonucleosides by Sequential Regioselective Reactions of 2,4-Dichloropyrimidine Nucleosides[J]. European Journal of Organic Chemistry, 2010. DOI:10.1002/ejoc.201000164.
[5] Kenji Yoshida, M. Taguchi. “Reaction of N-substituted cyclic amines with 2,4-dichloroquinazoline, 2,4-dichloropyrimidine, and its 5-methyl derivative.” Journal of The Chemical Society-perkin Transactions 1 102 1 (1992): 919–922.
[6] Samantha C Anderson, Scott T Handy. “One-pot Double Suzuki Couplings of Dichloropyrimidines.” Synthesis-Stuttgart 2010 16 (2010): 2721–2724.

2,4-Dichloropyrimidine

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