Alogliptin Related Compound 24 synthesis
- Product Name:Alogliptin Related Compound 24
- CAS Number:1430222-06-2
- Molecular formula:C14H12ClN3O2
- Molecular Weight:289.72
![2-[(6-CHLORO-2,4-DIOXO-3,4-DIHYDROPYRIMIDIN-1(2H)-YL)METHYL]BENZONITRILE](/CAS/GIF/865758-95-8.gif)
Yield:1430222-06-2 20%
Reaction Conditions:
with sodium hydride in tetrahydrofuran;dimethyl sulfoxide;
Steps:
Compound 2 (150 mg, 0.57 mmol) in THF-DMSO (6:1, 4mL) was treated with 60% NaH (26 mg, 0.65 mmol), followed by adding ethyl bromide (300uL). In a sealed tube, ~20% crude product in dry MeOH (3 mL) was treated NaHCO3 and ethane-1,2-diamine (200μL) at 120 °C for 2h, and purified by LC-MS to give the title compound 16. 1H-NMR (400 MHz, CDCl3-CD3OD 10:1) δ 7.70 (d, J=7.8 Hz, 1 H), 7.58 (t, J=7.7 Hz, 1 H), 7.40 (t, J=7.4 Hz, 1 H), 7.12 (d, J=8.1 Hz, 1 H), 5.37 (s, 2 H), 3.95 (q,J=6.8 Hz, 2 H), 3.45 (t, J=5.9 Hz, 2 H), 3.11 (t, J=6.1 Hz, 2 H), 1.19 (t, J=6.8 Hz, 3 H). MS (ES) [m+H] calc'd for C16H20N5O2, 314.2; found 314.2.
References:
EP1586571,2005,A1 Location in patent:Page/Page column 48
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