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

Melting point:

136.0 to 140.0 °C

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

form 

powder to crystal

pka

-0.72±0.40(Predicted)

color 

White to Almost white

InChI

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

InChIKey

AQECFYPZMBRCIA-UHFFFAOYSA-N

SMILES

C1(Cl)=NC(Cl)=C2SC=CC2=N1

Safety Information

Safety Statements 

24/25

RIDADR 

UN2811

HazardClass 

IRRITANT

HS Code 

29335990

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

Chemical Properties

2,4-Dichlorothieno[3,2-d]pyrimidine is White solid

Uses

2,4-Dichlorothieno[3,2-d]pyrimidine is used in the synthesis of PI3K inhibitor under noncryogenic conditions.

Synthesis

General procedure for the synthesis of 2,4-dichlorothieno[3,2-d]pyrimidine from thieno[3,2-d]pyrimidine-2,4-dione: To a suspension of thieno[3,2-d]pyrimidine-2,4-dione (5 g, 29 mmol) in POCl3 (40 mL) was added diisopropylethylamine (13 mL, 74 mmol), and the reaction mixture was heated refluxed for 2 hours. Upon completion of the reaction, the excess POCl3 and diisopropylethylamine were removed by distillation under reduced pressure. The resulting brown solid was dissolved in chloroform followed by aqueous phase partitioning. The aqueous phase was adjusted to alkaline by adding 5 M NaOH solution and extracted twice with chloroform. The organic phases were combined, washed sequentially with water and brine, dried over anhydrous Na2SO4 and filtered, and concentrated to afford the target product 2,4-dichlorothieno[3,2-d]pyrimidine as a light brown solid (6.05 g, quantitative yield).1H NMR (CDCl3, 300 MHz): δ 8.16 (d, J = 5.4 Hz, 1H), 7.56 (d, J = 5.7 Hz, 1H); LRMS (ESI): m/z calculated values [M + H]+ 204.94, 206.94, measured values 205.1, 207.0.

References

[1] Patent: WO2009/62258, 2009, A1. Location in patent: Page/Page column 91
[2] Patent: WO2005/49033, 2005, A1. Location in patent: Page/Page column 108
[3] Organic Process Research and Development, 2013, vol. 17, # 1, p. 97 - 107
[4] Patent: WO2011/79231, 2011, A1. Location in patent: Page/Page column 82
[5] Patent: JP6120311, 2017, B2. Location in patent: Paragraph 0130-0131

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