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 | Tert-butyl 2-chloro-4-morpholino-5H-pyrrolo[3,4-D]pyrimidine-6(7H)-carboxylate | HCID 71540665 | — |
| Solvent | CPME EtOH Water | HCID 131731673 | — |
| Product | HCID 46912801 | HCID 46912801 | 67% |
Reaction Steps
To a solution of tert-butyl 2-chloro-4-morpholino-5H-pyrrolo[3,4-d]pyrimidine-6(7H)-carboxylate (intermediate 2) (300 mg, 0.88 mmol) and 4-(3-ethylureido)phenylboronic acid pinacol ester (281 mg, 0.97 mmol) in CPME/EtOH/H2O (7/2/3) (4.0 mL) was added Pd(PPh3)2(Cl)2 (31 mg, 0.04 mmol) and Na2CO3 (140 mg, 1.32 mmol). The reaction mixture was then heated by microwave at 130° C. for 0.5 h. The crude reaction mixture was then partitioned between water and EtOAc, the phases separated and the solvent removed in vacuo. The residue was purified by flash chromatography (0-40% EtOAc/Petroleum Ether 40-60) to yield an off-white solid (275 mg, 67%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08785457B2 |
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| Source dataset | uspto-grants-2014_07 |
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| ORD ID | ord-fa4fea665caa4df599a9db83577ddf14 |
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| Source note | uspto-grants-2014_07 |
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