8-Bromo-7-but-2-ynyl-3-methyl-1-(4-methyl-quinazolin-2-ylmethyl)-3,7-dihydro-purine-2,6-dione Chemical Properties

Melting point:

>255°C (dec.)

Boiling point:

602.9±65.0 °C(Predicted)

Density 

1.55

storage temp. 

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

solubility 

DMSO (Slightly, Heated, Sonicated), Methanol (Very Slightly, Heated, Sonicated)

pka

2.34±0.50(Predicted)

form 

Solid

color 

White to Pale Yellow

InChI

InChI=1S/C20H17BrN6O2/c1-4-5-10-26-16-17(24-19(26)21)25(3)20(29)27(18(16)28)11-15-22-12(2)13-8-6-7-9-14(13)23-15/h6-9H,10-11H2,1-3H3

InChIKey

RCZJXCXNYGHNSR-UHFFFAOYSA-N

SMILES

N1(CC#CC)C2=C(N(C)C(=O)N(CC3=NC(C)=C4C(=N3)C=CC=C4)C2=O)N=C1Br

8-Bromo-7-but-2-ynyl-3-methyl-1-(4-methyl-quinazolin-2-ylmethyl)-3,7-dihydro-purine-2,6-dione Usage And Synthesis

Uses

8-Bromo-7-(2-butyn-1-yl)-3,7-dihydro-3-methyl-1-[(4-methyl-2-quinazolinyl)methyl]-1H-purine-2,6-dione is an intermediate used to prepare selective inhibitors of dipeptidyl peptidase 4 (DPP4) for potential use in the treatment of type 2 diabetes.

Synthesis

General procedure: 3-methyl-7-(2-butyn-1-yl)-8-bromoxanthine (Compound VII, 1.34 g, 4.5 mmol), potassium carbonate (1.42 g, 10.3 mmol), 2-chloromethyl-4-methylquinazoline (Compound III, 0.87 g, 4.5 mmol), tributylmethylammonium chloride (phase transfer catalyst, 0.53 g , 2 mmol) and 2-methyltetrahydrofuran (50 mL) were added sequentially to the reaction flask. The reaction mixture was heated to reflux and maintained for 3 to 5 hours. Upon completion of the reaction, it was cooled to room temperature and the reaction was quenched by the addition of water (100 mL). The reaction mixture was filtered, the filter cake was collected and dried at 45 °C to afford 1-[(4-methylquinazolin-2-yl)methyl]-3-methyl-7-(2-butyn-1-yl)-8-bromoxanthine (Compound VIII). Yield: 1.78 g (87.1% yield). Mass spectrum (MS): [M + H]+ = 453/455. 1H-NMR (400 MHz, DMSO-d6): δ 1.79 (t, J = 2.3 Hz, 3H), 2.89 (s, 3H), 3.44 (s, 3H), 5.11 (q, J = 2.2 Hz, 2H), 5.35 (s, 2H), 7.67 (m, 1H), 7.80 (d, J = 8.3 Hz, 1H), 7.75 ( m, 1H), 8.24 (d, J = 8.1 Hz, 1H).

References

[1] Patent: WO2005/51950, 2005, A1. Location in patent: Page/Page column 18
[2] Patent: US2015/274728, 2015, A1. Location in patent: Paragraph 0070-0074
[3] Patent: WO2015/87240, 2015, A1. Location in patent: Page/Page column 12
[4] Patent: , 2016, . Location in patent: Paragraph 0045; 0046; 0047; 0048
[5] Patent: CN105936634, 2016, A. Location in patent: Paragraph 0064; 0065; 0066; 0067

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