HuagongsheHuagongshe Chemistry Print Report · For research reference only
Potassium Carbonate → 5-[2-(3,4-Dimethoxy-phenyl)-6-methyl-imidazo[2,1-b][1,3,4]thiadiazol-5-yl]-pyrimidin-2-ylamine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | 2-Aminopyrimidine-5-boronic acid, pinacol ester | HCID 17750212 | — |
| Reactant | 2-(3,4-Dimethoxy-phenyl)-5-iodo-6-methyl-imidazo[2,1-b][1,3,4]thiadiazole | HCID 66716939 | — |
| Catalyst | HCID 178418476 | HCID 178418476 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | 5-[2-(3,4-Dimethoxy-phenyl)-6-methyl-imidazo[2,1-b][1,3,4]thiadiazol-5-yl]-pyrimidin-2-ylamine | HCID 66717058 | 31.9% |
Reaction Steps
A mixture of 2-(3,4-dimethoxy-phenyl)-5-iodo-6-methyl-imidazo[2,1-b][1,3,4]thiadiazole (0.041 g, 0.102 mmol, 1 eq), 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidin-2-amine (0.056 g, 0.255 mmol, 2.5 eq), Pd(Ph3P)2Cl2 (0.007 g, 0.0102 mmol, 0.1 eq) and potassium carbonate (0.07 g, 0.51 mmol, 5 eq) in water (0.3 mL) and dioxane (2.2 mL) was subjected to MW irradiation (120° C., 35 min, 200 W). The solvents were evaporated, and the residue obtained was purified by silica gel chromatography (0-3% MeOH in DCM) and preparative HPLC (RP-C18, ACN/water) to give the desired product (0.012 g). HPLC-MS: (5-100% B in 8 min, 0.8 mL/min, 50° C.): tR=4.08 min, [M+H]+ m/z 369.1
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08815918B2 |
| Source dataset | uspto-grants-2014_08 |
| ORD ID | ord-85970143b37d4ba5992c7c511043c498 |
| Source note | uspto-grants-2014_08 |