2,4-Dichlorothieno[2,3-d]pyrimidine Chemical Properties

Boiling point:

274.8±22.0 °C(Predicted)

Density 

1.662±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

pka

-0.84±0.40(Predicted)

form 

crystalline powder

color 

Pale yellow

InChI

InChI=1S/C6H2Cl2N2S/c7-4-3-1-2-11-5(3)10-6(8)9-4/h1-2H

InChIKey

HRXNGIQKOWQHCX-UHFFFAOYSA-N

SMILES

C1(Cl)=NC(Cl)=C2C=CSC2=N1

Safety Information

Risk Statements 

36

Safety Statements 

26

RIDADR 

2811

HazardClass 

6.1

PackingGroup 

Ⅲ

HS Code 

2934999090

Storage Class

6.1C - Combustible acute toxic Cat.3
toxic compounds or compounds which causing chronic effects

Hazard Classifications

Acute Tox. 3 Oral
Eye Irrit. 2

2,4-Dichlorothieno[2,3-d]pyrimidine Usage And Synthesis

Application

2,4-Dichlorothiophene[2,3-D]pyrimidine is an organic intermediate commonly used in the preparation of pharmaceutical products.

Synthesis

General procedure for the synthesis of 2,4-dichlorothieno[2,3-d]pyrimidines from 2,4-dihydroxythieno[2,3-d]pyrimidines: thieno[2,3-d]pyrimidine-2,4(1H,3H)-dione (12) (2.5 g, 0.012 mol) and a drop of N,N-dimethylformamide (DMF) were added to 20 mL phosphorus oxychloride (POCl3) . The reaction mixture was heated to 115°C and kept for 8 hours. After the reaction was completed, it was cooled to room temperature and the reaction mixture was slowly poured into 500 g of ice-water mixture. The solid product was collected by filtration and dissolved in dichloromethane (CH2Cl2). The insoluble material was removed by filtration and the filtrate was distilled under reduced pressure to give 1.7 g of 2,4-dichlorothieno[2,3-d]pyrimidine (13) in 56.0% yield. The structure of the product was confirmed by 1H NMR (400 MHz, DMSO-d6) δ 8.16 (d, J = 3.4 Hz, 1H, Ar-H), 7.62 (d, J = 3.4 Hz, 1H, Ar-H) and ESI-MS (m/z): 205.1 [M+H]+.

References

[1] Journal of Medicinal Chemistry, 2011, vol. 54, # 22, p. 7815 - 7833
[2] Bulletin of the Korean Chemical Society, 2010, vol. 31, # 8, p. 2242 - 2246
[3] European Journal of Medicinal Chemistry, 2015, vol. 93, p. 64 - 73
[4] Patent: CN106831812, 2017, A. Location in patent: Paragraph 0091; 0092; 0093
[5] Patent: JP6120311, 2017, B2. Location in patent: Paragraph 0144-0145

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