Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Methanol | HCID 887 | — |
| Reactant | Iodobenzene | HCID 11575 | — |
| Reactant | Potassium Phosphate, Tribasic | HCID 62657 | — |
| Reactant | (2,4-Dimethoxypyrimidin-5-yl)boronic acid | HCID 2736209 | — |
| Catalyst | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| Solvent | Dimethyl Sulfoxide | HCID 679 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | 2,4-Dimethoxy-5-phenylpyrimidine | HCID 57498037 | 75% |
Reaction Steps
To 2,4-Dimethoxypyrimidine-5-boronic acid (200 mg, 10.6 mmol), Iodobenzene (326 mg, 1.60 mmol) and K3PO4 (900 mg, 4.24 mmol) in DMSO (5 mL, purged with Ar) was added 1,1′bis(diphenylphosphino)ferrocene palladium chloride, complex with dichloromethane (12 mg) and the reaction solution was heated to 60 C in a sealed tube. The solution was heated for 2 h, stirred at room temperature for 10 hr and filtered through celite. The solution was poured into sat. NaHCO3 to give a gray solid. This material was collected, dissolved in ethyl acetate, dried (Na2SO4). Flash chromatography 0 to 2% methanol in dichloromethane gave 2,4-Dimethoxy-5-phenyl-pyrimidine (171 mg, 75% yield). HPLC tr=5.62 min (83%), FIA m/e 217.2 (M+H), HNMR (500 MHz, CDCl3) 8.25 (1H, s), 7.45-7.29 (5H, m), 4.00 (3H, s), 3.98 (3H, s).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US07842712B2 |
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| Source dataset | uspto-grants-2010_11 |
|---|
| ORD ID | ord-b1a5f93a92b8442091999cc9538dd97a |
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| Source note | uspto-grants-2010_11 |
|---|
