8-bromo-7-(but-2-ynyl)-3-methyl-1H-purine-2,6(3H,7H)-dione Chemical Properties

Melting point:

285 °C

Density 

1.71

storage temp. 

2-8°C

solubility 

DMSO (Slightly), Methanol (Slightly)

form 

powder to crystal

pka

8.91±0.70(Predicted)

color 

White to Almost white

Major Application

pharmaceutical small molecule

InChI

InChI=1S/C10H9BrN4O2/c1-3-4-5-15-6-7(12-9(15)11)14(2)10(17)13-8(6)16/h5H2,1-2H3,(H,13,16,17)

InChIKey

HFZOBQSHTNNKFY-UHFFFAOYSA-N

SMILES

N1(CC#CC)C2=C(N(C)C(=O)NC2=O)N=C1Br

LogP

1.25 at 20℃

CAS DataBase Reference

666816-98-4

Safety Information

HS Code 

2933.99.8290

8-bromo-7-(but-2-ynyl)-3-methyl-1H-purine-2,6(3H,7H)-dione Usage And Synthesis

Application

8-Bromo-7-(2-Butynedi)-3-methylxanthine is an intermediate in the synthesis of liraristine and can be used in pharmaceutical research. It is an intermediate in organic synthesis.

Chemical Properties

White powder

Uses

This Certified Reference Material (CRM) is produced and certified in accordance with ISO 17034 and ISO/IEC 17025. All information regarding the use of this CRM can be found on the certificate of analysis.

Synthesis

8-bromo-3-methyl-3,7-dihydro-1H-purine-2,6-dione (2.450 g, 10 mmol),1-bromo-2-butyne (1.596 g, 12 mmol), Sodium carbonate (1.590 g, 15 mmol), and 20mL of acetone was added to a 100mL flask. The reaction system was heated to 40 ° C, and the reaction was stirred for 4h. After the reaction was cooled to room temperature, suction filtration was performed, and the filter cake was washed with methanol to obtain a crude product as a pale yellow solid. The crude product was reconstituted with dichloromethane and cyclohexane. Yield 2.912 g of 8-bromo-7-(but-2-ynyl)-3-methyl-1H-purine-2,6(3H,7H)-dione. The yield was 98%, and the purity was 99.9%.

References

[1] Patent: US2015/274728, 2015, A1. Location in patent: Paragraph 0056-0060
[2] Patent: , 2016, . Location in patent: Paragraph 0097;0098
[3] Patent: WO2014/97314, 2014, A1. Location in patent: Page/Page column 9
[4] Patent: CN104292228, 2016, B. Location in patent: Paragraph 0057-0058; 0089-0092
[5] Journal of Medicinal Chemistry, 2007, vol. 50, # 26, p. 6450 - 6453

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