Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | N-Ethyl-N'-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]urea | HCID 44119377 | — |
| Reactant | Pyrido[3,4-d]pyriMidine-7(6H)-carboxylic acid, 2-chloro-5,8-dihydro-4-[(3S)-3-Methyl-4-Morpholinyl]-, 1,1-diMethylethyl ester | HCID 59239275 | — |
| Solvent | Dimethoxyethane ethanol water | HCID 86587095 | — |
| Product | HCID 59239149 | HCID 59239149 | 59.4% |
Reaction Steps
To a solution of (S)-tert-butyl 2-chloro-4-(3-methylmorpholino)-5,6-dihydropyrido[3,4-d]pyrimidine-7(8H)-carboxylate (intermediate 4) (576 mg, 1.56 mmol) and 4-(3-ethylureido)phenylboronic acid pinacol ester (498 mg, 1.72 mmol) in DME/EtOH/H2O (12/5/3) (15 mL) was added Pd(PPh3)2(Cl)2 (55 mg, 0.078 mmol) and Na2CO3 (496 mg, 4.68 mmol). The reaction mixture was then heated by microwave at 120° C. for 1 h. The crude reaction mixture was then partitioned between water and EtOAc, the phases separated and the organic layer washed with aqueous NaHCO3 and brine, dried over magnesium sulfate, filtered and the solvent removed in vacuo. The residue was purified by flash chromatography (20-50% EtOAc/Petroleum Ether 40-60) to yield a yellow solid (460 mg, 59%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08785457B2 |
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| Source dataset | uspto-grants-2014_07 |
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| ORD ID | ord-76deec4061e542ffb62dc757fa2245bd |
|---|
| Source note | uspto-grants-2014_07 |
|---|
