Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Methanol | HCID 887 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | HCID 43600040 | HCID 43600040 | — |
| Reactant | 2,4-Dichloro-N-methyl-5-pyrimidinecarboxamide | HCID 57827010 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Solvent | N-methyl-2-pyrrolidone | HCID 13387 | — |
| Product | HCID 86729631 | HCID 86729631 | — |
Reaction Steps
To a solution of 2,4-dichloro-N-methylpyrimidine-5-carboxamide (400 mg, 1.95 mmol) in NMP (1 ml), N-(2-aminophenyl)acrylamide (316 mg, 1.951 mmol) and DIPEA (503 mg, 3.902 mmol) were added and heated at 120° C. for 1 h. TLC showed completion of starting material (TLC system: 5% methanol in DCM (Rf): 0.3). The reaction mixture was diluted with water (30 ml) and extracted with ethyl acetate (3×15 ml). The organic layer was separated, dried over sodium sulphate, and concentrated. Crude compound was purified by column chromatography using silica gel (100-200 mesh) with 2% methanol in DCM to obtain 4-(2-acrylamidophenylamino)-2-chloro-N-methylpyrimidine-5-carboxamide as an off white solid. Yield: (180 mg, 28%). MS: m/z 332.1 (ES+, M+H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09145387B2 |
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| Source dataset | uspto-grants-2015_09 |
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| ORD ID | ord-6a37e81c9a374911a0bf4763257fb66d |
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| Source note | uspto-grants-2015_09 |
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