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

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

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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