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

Product Name2,4-Dichlorothieno[3,2-d]pyrimidine
CAS16234-14-3
MFC6H2Cl2N2S
MW205.06
EINECS695-110-4
MOL File16234-14-3.mol

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
WGK Germany	WGK 3
HazardClass	IRRITANT
HS Code	29335990
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

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

1,3-Dihydrothiopheno[3,2-d]pyrimidine-2,4-dione

16233-51-5

16234-14-3

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

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

Chemical Properties

Safety Information

Usage And Synthesis

Preparation Products And Raw materials

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