Sodium Iodide → Ethyl 6-(2-ethoxy-2-oxoethyl)-7-iodo-5-methylpyrazolo[1,5-a]pyrimidine-2-carboxylate
Reaction equation
Cl[C:2]1[N:7]2[N:8]=[C:9]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:10]=[C:6]2[N:5]=[C:4]([CH3:16])[C:3]=1[CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19].[I-:23].[Na+]>C(#N)C>[CH2:21]([O:20][C:18](=[O:19])[CH2:17][C:3]1[C:4]([CH3:16])=[N:5][C:6]2[N:7]([N:8]=[C:9]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:10]=2)[C:2]=1[I:23])[CH3:22]Participants
Conditions
- Temperature
- 80 °C
Procedure
Ethyl 7-chloro-6-(2-ethoxy-2-oxoethyl)-5-methylpyrazolo[1,5-a]pyrimidine-2-carboxylate (5 g, 15.35 mmol) and sodium iodide (9.20 g, 61.4 mmol) were suspended in acetonitrile (80 mL) and the resulting mixture was heated at 80° C. for 2 h. At this point LCMS indicated completion of the reaction and appearance of the desired product. After cooling to rt, the reaction mixture was diluted with ethyl acetate and washed with water and aqueous Na2S2O3. The organic phase was dried (Na2SO4), filtered and concentrated in vacuo. The crude product was triturated with ethyl acetate/hexane to afford ethyl 6-(2-ethoxy-2-oxoethyl)-7-iodo-5-methylpyrazolo[1,5-a]pyrimidine-2-carboxylate (5.7 g, 13.7 mmol, 89% yield) as an off-white solid. 1H NMR (500 MHz, CDCl3) δ 7.32 (s, 1H), 4.51 (d, J=7.0 Hz, 2H), 4.25 (d, J=7.0 Hz, 2H), 4.02 (s, 2H), 2.68 (s, 3H), 1.48 (t, J=7.2 Hz, 3H), 1.31 (t, J=7.2 Hz, 3H). LCMS (M+H)=418.2.
Sources & evidence
- ORD record
- ord-731af98a5c454a229e4f7a7f23d8cf77
- Source dataset
- uspto-grants-2015_04
- Patent number
- US09006235B2
Reaction notes
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