8-Bromo-3-methyl-xanthine Chemical Properties

Melting point:

300°C(lit.)

Density 

1.974

storage temp. 

under inert gas (nitrogen or Argon) at 2–8 °C

solubility 

DMF (Slightly), DMSO (Slightly)

form 

powder to crystal

pka

7.65±0.20(Predicted)

color 

White to Almost white

InChI

InChI=1S/C6H5BrN4O2/c1-11-3-2(8-5(7)9-3)4(12)10-6(11)13/h1H3,(H,8,9)(H,10,12,13)

InChIKey

QTEQVEJOXGBDGI-UHFFFAOYSA-N

SMILES

N1C2=C(N(C)C(=O)NC2=O)NC=1Br

Safety Information

Risk Statements 

22

Safety Statements 

26-36/37/39

HS Code 

29339900

8-Bromo-3-methyl-xanthine Usage And Synthesis

Chemical Properties

Light yellow solid

Uses

8-Bromo-3,9-dihydro-3-methyl-1H-purine-2,6-dione, is a substituted derivative of Xanthine (X499950), found in animal organs, yeast, potatoes, coffee beans, tea. It can also be used for the synthesis of Linagliptin (L465900), which is a novel potent and selective dipeptidyl peptidase-4 (DPP-4) inhibitor with potential use in the treatment of type 2 diabetes.

Synthesis

Step 1: Synthesis of 8-bromo-3-methyl-3,7-dihydro-1H-purine-2,6-dione 3-Methyl-3,7-dihydro-1H-purine-2,6-dione (11.3 g, 6.8 mmol) was dissolved in acetic acid (300 mL) and sodium acetate (8.37 g, 13.6 mmol) was added. Subsequently, bromine (13.04 g, 8.2 mmol) was added slowly dropwise at 50 °C. After the dropwise addition was completed, the reaction mixture was warmed up to 65 °C with continuous stirring for 3 hours. After completion of the reaction, the mixture was cooled to room temperature and slowly poured into ice water (500 g) to precipitate the product. The precipitate was collected by filtration and the filter cake was washed twice with cold water and finally dried under vacuum to give 8-bromo-3-methyl-3,7-dihydro-1H-purine-2,6-dione (16.1 g, 96.6% yield) as a light yellow solid.LCMS analysis showed a retention time of 0.541 min; LCMS (MH+) m/z: 245.

References

[1] Patent: WO2014/143799, 2014, A2. Location in patent: Page/Page column 371
[2] Patent: WO2014/97314, 2014, A1. Location in patent: Page/Page column 3; 8-9; 15
[3] Patent: US2002/28823, 2002, A1
[4] Patent: US2002/103211, 2002, A1
[5] Patent: US6774130, 2004, B2

8-Bromo-3-methyl-xanthine(93703-24-3)Related Product Information

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• 8-AZAGUANINE
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• 2,6-Dichloropurine
• 2,6-Diaminopurine