Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | 1,4-Dioxane | HCID 31275 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | 4-(7-bromo-3-methyl-3,4-dihydroisoquinolin-2(1H)-yl)-6-(4-methylpiperazin-1-yl)pyrimidin-2-amine | HCID 59402317 | — |
| Reactant | HCID 59402346 | HCID 59402346 | — |
| Catalyst | HCID 178418397 | HCID 178418397 | — |
| Solvent | Methanol | HCID 887 | — |
| Solvent | Water | HCID 962 | — |
| Product | HCID 68472901 | HCID 68472901 | 59.3% |
Reaction Steps
A mixture of 4-(7-bromo-3-methyl-3,4-dihydroisoquinolin-2(1H)-yl)-6-(4-methylpiperazin-1-yl)pyrimidin-2-amine (10 mg, 0.02 mmol; Peak 1, Example 49, Step 7), 1-(tetrahydrofuran-2-ylmethyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (7.3 mg, 0.026 mmol), tetrakis(triphenylphosphine)palladium(0) (1.4 mg, 0.0012 mmol) and sodium bicarbonate (6.0 mg, 0.072 mmol) in a solution of 1,4-dioxane (0.2 mL) and water (0.1 mL) in a reaction vial was stirred at 90° C. overnight. After cooling it was diluted with methanol. The solid was filtered off. The filtrate was purified with RP-HPLC (pH=10) to afford the desired product (5.8 mg). LCMS (M+H)+: m/z=489.4.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08436008B2 |
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| Source dataset | uspto-grants-2013_05 |
|---|
| ORD ID | ord-b7f53e0ba818484e8c9979cdbbbf63c1 |
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| Source note | uspto-grants-2013_05 |
|---|