Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Potassium Phosphate, Tribasic | HCID 62657 | — |
| Reactant | 4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine | HCID 2734648 | — |
| Reactant | HCID 59244794 | HCID 59244794 | — |
| Catalyst | palladium(II) acetate | HCID 167845 | — |
| Catalyst | 2-Dicyclohexylphosphino-2',6'-dimethoxybiphenyl | HCID 11269872 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 59244400 | HCID 59244400 | 112.9% |
Reaction Steps
1-(4-Chloro-2-morpholin-4-yl-5,6-dihydro-pyrrolo[2,3-d]pyrimidin-7-yl)-ethanone (J-01-D, 217 mg), 4-(4,4,5,5-tetramethyl-[1,3]dioxaborolan-2-yl)-pyridine (189 mg), palladium acetate (8.6 mg), S-Phos (32 mg) and potassium phosphate (326 mg) were suspended in DMF (7.6 ml), followed by stirring at 100° C. for 3 hours. To the reaction mixture, water (50 ml) was added, followed by extraction five times with ethyl acetate/THF (40 ml/10 ml). The combined extracts were washed with saturated aqueous sodium chloride solution, followed by drying over sodium sulfate. After the sodium sulfate was filtered off, the filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (dichloromethane/methanol=100/0 to 50/1), to obtain the desired compound (D-323) as a pale yellow powder (282 mg, 100%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08022205B2 |
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| Source dataset | uspto-grants-2011_09 |
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| ORD ID | ord-bc69495e0c644c93a7ed5831558fd820 |
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| Source note | uspto-grants-2011_09 |
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