HuagongsheHuagongshe Chemistry Print Report · For research reference only
Ethyl Acetate → Ethyl 4-methyl-2-(1-methylpyrazol-4-yl)pyrimidine-5-carboxylate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Ethyl Acetate | HCID 8857 | — |
| Reactant | Potassium Phosphate, Tribasic | HCID 62657 | — |
| Reactant | 1-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole | HCID 2773987 | — |
| Reactant | Ethyl 2-chloro-4-methylpyrimidine-5-carboxylate | HCID 21220624 | — |
| Catalyst | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | Ethyl 4-methyl-2-(1-methylpyrazol-4-yl)pyrimidine-5-carboxylate | HCID 102972407 | 32% |
Reaction Steps
Ethyl 2-chloro-4-methylpyrimidine-5-carboxylate (1.0 g, 5.0 mmol), 1-methyl-4-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (1.24 g, 6.0 mmol), K3PO4 (3.18 mg, 15.0 mmol) and Pd(dppf)Cl2 (100 mg) in dioxane (15 mL) and H2O (3 mL) were heated at 120° C. for 18 h under N2. Silica gel chromatography (PE:EA=3:1 to 1:1) gave the title compound (72 mg, yield: 32.0%). 1H NMR (CDCl3, 400 MHz) δ 9.08 (s, 1H), 8.22 (s, 1H), 8.15 (s, 1H), 4.40 (q, J=7.2 Hz, 2H), 3.98 (s, 3H), 2.82 (s, 3H), 1.42 (t, J=7.2 Hz, 3H). LCMS: 247.1 (M+1)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09034900B2 |
| Source dataset | uspto-grants-2015_05 |
| ORD ID | ord-9e17c4cf8b0a436c94b0f7760f4c757b |
| Source note | uspto-grants-2015_05 |