2-Amino-4,6-dichloropyrimidine

2-Amino-4,6-dichloropyrimidine Property

Melting point:

219-222 °C (lit.)

Boiling point:

219-222°C

Density 

1.6662 (rough estimate)

refractive index 

1.6300 (estimate)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

pka

0.14±0.10(Predicted)

form 

Liquid

color 

Clear colorless to light yellow

Water Solubility 

Insoluble in water, soluble in acetone, two monomer (VCM) and thermal toluene.

BRN 

118454

InChI

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

InChIKey

JPZOAVGMSDSWSW-UHFFFAOYSA-N

SMILES

C1(N)=NC(Cl)=CC(Cl)=N1

CAS DataBase Reference

56-05-3(CAS DataBase Reference)

EPA Substance Registry System

2-Pyrimidinamine, 4,6-dichloro- (56-05-3)

Safety

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36-24/25

WGK Germany 

3

RTECS 

UV6260485

F 

10

TSCA 

T

HazardClass 

IRRITANT

HS Code 

29335995

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

2-Amino-4,6-dichloropyrimidine Chemical Properties,Usage,Production

Chemical Properties

LIGHT BROWN CRYSTALLINE POWDER

Uses

Microwave-assisted synthesis of pyrazolo [3, 4-d] pyrimidines from 2-amino-4, 6-dichloropyrimidine-5-carbaldehyde is under solvent-free conditions. A series of 6-alkynyl-2,4-diaminopyrimidine derivatives bearing various substituents at alkynyl moiety was prepared by the Sonogashira cross-coupling reaction of 2,4-diamino-6-iodopyrimidine using Pd(PPh3)2Cl2 as catalyst.

Synthesis

The general procedure for the synthesis of 2-amino-4,6-dichloropyrimidine from 2-amino-4,6-dihydroxypyrimidine is as follows: in a four-necked flask equipped with a reflux condenser, 510 g of 2-amino-4,6-dihydroxypyrimidine (98% purity, 4 mol) and 1428 g of phosphorus triclosan (99% purity) were added, heated and stirred. 810 g of triethylamine (99% purity) was slowly added dropwise at 40 to 45 °C through a constant pressure dropping funnel. After the dropwise addition, the reaction temperature was raised to 85 to 90 °C and maintained at this temperature for 2 hours. The progress of the reaction was monitored by high performance liquid chromatography (HPLC) and the reaction was considered complete when the amount of 2-amino-4,6-dihydroxypyrimidine was less than 1%. Subsequently, 3000 g of toluene was added to the reaction mixture, cooled to 0-10°C, and 3000 g of ice-water mixture was added for low temperature hydrolysis. The mixture was then warmed to room temperature and left to stratify. The aqueous layer was extracted twice with 400 g of toluene, and the organic phases were combined and washed sequentially with aqueous sodium carbonate and water until neutral. The organic phase was concentrated and 1800 g of toluene was recovered to give 2668 g of highly concentrated toluene solution. The product was analyzed by HPLC, the purity was 96.8%, the content was 22.58% (external standard method), and the yield of crude product was 92%.

References

[1] Patent: CN108395409, 2018, A. Location in patent: Paragraph 0046-0047; 0050
[2] Organic Letters, 2009, vol. 11, # 1, p. 61 - 64
[3] Chemical Communications, 2017, vol. 53, # 18, p. 2689 - 2692
[4] Organic and Biomolecular Chemistry, 2017, vol. 15, # 47, p. 10087 - 10094
[5] Tetrahedron Letters, 2015, vol. 56, # 10, p. 1179 - 1182