Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Methyl iodide | HCID 6328 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | HCID 178515245 | HCID 178515245 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Product | HCID 57898046 | HCID 57898046 | 99.2% |
Reaction Steps
To a solution of 5-(4-chloro-phenyl)-1-phenyl-6-[4-(1H-pyrazol-3-yl)-phenyl]-1,5-dihydro-pyrazolo[3,4-d]pyrimidin-4-one (4 mg, 0.008 mmol) in MeCN (0.5 mL) is added K2CO3 (5 mg) followed by MeI (0.05 mL). The mixture is heated to 60° C. for 16 h and then cooled down to room temperature. The reaction mixture is then treated with water (3 mL) and extracted with EtOAc. The combined extracts is concentrated and purified by preparative thin layer chromatography (silica gel, 30% EtOA/hexane) to provide the title compound 5-(4-chloro-phenyl)-6-[4-(1-methyl-1H-pyrazol-3-yl)-phenyl]-1-phenyl-1,5-dihydro-pyrazolo[3,4-d]pyrimidin-4-one as white solid (3.8 mg, 92%). 1H NMR (CDCl3) δ (ppm) 8.33(s, 1H), 8.17(d, 2H), 7.70(d, 2H), 7.51(t, 2H), 7.38 (m, 4H), 7.11(d, 2H), 6.54(d, 1H), 3.97(s, 3H). HPLC-MS calculated C27H19ClN6O (M+1+): 479.1. Found: 479.1.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08158634B2 |
|---|
| Source dataset | uspto-grants-2012_04 |
|---|
| ORD ID | ord-d2e9dc252bf9424cb0055b9fe164877f |
|---|
| Source note | uspto-grants-2012_04 |
|---|