Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | P-Anisidine | HCID 7732 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | Potassium Fluoride | HCID 522689 | — |
| Reactant | 4-(Benzylamino)-2-(methanesulfonyl)pyrimidine-5-carboxamide | HCID 23071581 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | N-methyl-2-pyrrolidone | HCID 13387 | — |
| Product | HCID 67388964 | HCID 67388964 | 24% |
Reaction Steps
A 5 ml portion of NMP solution containing 300 mg of 4-benzylamino-2-(methylsulfonyl)pyrimidine-5-carboxamide was mixed with 122 mg of p-anisidine and 58 mg of potassium fluoride, followed by stirring at 90 to 100° C. for 21 hours. During this period, 58 mg of potassium fluoride was added three times. The reaction mixture was cooled down to room temperature, diluted with water, mixed with saturated sodium bicarbonate aqueous solution and then extracted with ethyl acetate. The organic layer was washed with saturated brine, and then the solvent was evaporated. The resulting residue was purified by a silica gel column chromatography (chloroform:methanol) and then recrystallized (methanol-THF) to obtain 82 mg of 4-benzylamino-2-[(4-methoxyphenyl)amino]pyrimidine-5-carboxamide as colorless crystals.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08012959B2 |
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| Source dataset | uspto-grants-2011_09 |
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| ORD ID | ord-ee68f5f9bbb84651b13a5f58f5418765 |
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| Source note | uspto-grants-2011_09 |
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