Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Nitrogen | HCID 947 | — |
| Reactant | Potassium Phosphate, Tribasic | HCID 62657 | — |
| Reactant | 8-Bromo-6-methyl-2-(1-methylpyrazol-4-yl)pyrido[4,3-d]pyrimidin-5-one | HCID 118022310 | — |
| Reactant | 2-(5-Ethylsulfonyl-2-propoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane | HCID 123570089 | — |
| Catalyst | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | US10023592, Example 225 | HCID 118022134 | 83.3% |
Reaction Steps
The title compound of step 2 (60 mg, 0.17 mmol), the title compound of Example 224, step 4 (64 mg, 0.20 mmol), K3PO4 (108 mg, 0.51 mmol), and Pd(dppf)Cl2 (15 mg, 0.02 mmol) in dioxane (8 mL) were purged with N2 and heated at 70° C. for 18 h. CH2Cl2 extractive work up and preparative HPLC gave the title compound (66.11 mg, yield: 83.3%) as a grey solid. 1H NMR (CDCl3, 400 MHz) δ 9.64 (s, 1H), 8.19 (s, 1H), 8.12 (d, J=2.4 Hz, 1H), 8.06 (s, 1H), 7.96 (dd, J1=8.8 Hz, J2=2.4 Hz, 1H), 7.70 (s, 1H), 7.15 (d, J=8.4 Hz, 1H), 4.03-3.95 (m, 5H), 3.67 (s, 3H), 3.20 (q, J=7.2 Hz, 2H), 1.67-1.60 (m, 2H), 1.36 (t, J=7.2 Hz, 3H), 0.81 (t, J=7.2 Hz, 3H). LCMS: 468.2 (M+1)+
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US09034900B2 |
|---|
| Source dataset | uspto-grants-2015_05 |
|---|
| ORD ID | ord-2a823e2b511849f99572c7f471d7d08a |
|---|
| Source note | uspto-grants-2015_05 |
|---|
