Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Nitrogen | HCID 947 | — |
| Reactant | Potassium Phosphate, Tribasic | HCID 62657 | — |
| Reactant | 8-Bromo-6-methylpyrido[4,3-d]pyrimidin-5(6H)-one | HCID 118021926 | — |
| Reactant | 2-[2-(Cyclopropylmethoxy)-5-(methylsulfonyl)phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane | HCID 123434859 | — |
| Catalyst | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | US10023592, Example 231 | HCID 118022550 | 34.2% |
Reaction Steps
The title compound of step 3 (100 mg, 0.42 mmol), the title compound of Example 90, step 1 (147 mg, 0.42 mmol), Pd(dppf)Cl2 (62 mg, 0.08 mmol), K3PO4 (221 mg, 1.04 mmol) in dioxane (4 mL) and H2O (0.5 mL) was purged with N2 and heated at 100° C. for 18 h. Following CH2Cl2 extractive work up, silica gel chromatography (PE:EA=2:10:1) and preparative HPLC, the title compound (54.57 mg, yield: 34.2%) was obtained as a yellow solid. 1H NMR: (DMSO-d6, 400 MHz) δ: 9.54 (s, 1H), 9.30 (s, 1H), 8.18 (s, 1H), 7.93 (dd, J1=8.8 Hz, J2=2.4 Hz, 1H), 7.85 (d, J=2.4 Hz, 1H), 7.31 (d, J=8.8 Hz, 1H), 3.91 (d, J=6.8 Hz, 2H), 3.61 (s, 3H), 3.20 (s, 3H), 0.94-0.92 (m, 1H), 0.35-0.30 (m, 2H), 0.10-0.06 (m, 2H). LCMS: 386.0 (M+H)+
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US09034900B2 |
|---|
| Source dataset | uspto-grants-2015_05 |
|---|
| ORD ID | ord-a3dbcae969354f388b53186e7dd4aebb |
|---|
| Source note | uspto-grants-2015_05 |
|---|
