Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | (4-Amino-3-methoxyphenyl)boronic acid | HCID 57473274 | — |
| Reactant | 2-Chloro-4-[(3S)-3-methylmorpholin-4-yl]-6-(methylsulfonylmethyl)pyrimidine | HCID 57547356 | — |
| Solvent | Ethanol | HCID 702 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | 1,2-Dimethoxyethane | HCID 8071 | — |
| Product | HCID 59380038 | HCID 59380038 | — |
Reaction Steps
2-Chloro-4-[(3S)-3-methylmorpholin-4-yl]-6-(methylsulfonylmethyl)pyrimidine (700 mg, 2.29 mmol) was dissolved in a solution of 18% DMF in a mixture of 7:3:2 DME:water:ethanol (7 mL). (4-Amino-3-methoxy-phenyl)boronic acid (574 mg, 3.43 mmol), 2M sodium carbonate solution (4 mL) and dichlorobis(triphenylphosphine) palladium (81 mg) was then added to the solution and refluxed at 90° C. for 1 hour. The reaction was allowed to cool to room temp then partitioned between ethyl acetate (50 mL) and water (50 mL), the organics dried over magnesium sulphate, filtered and concentrated in vacuo. The residue was dissolved in dichloromethane and filtered to remove insoluble material. The filtrates were purified using a companion.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07750003B2 |
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| Source dataset | uspto-grants-2010_07 |
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| ORD ID | ord-869c9bfe74a445f79eac7fde64780dca |
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| Source note | uspto-grants-2010_07 |
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