Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Dichloromethane | HCID 6344 | — |
| Reactant | 4-Fluorophenol | HCID 9732 | — |
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | HCID 71290072 | HCID 71290072 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 71283247 | HCID 71283247 | 50.5% |
Reaction Steps
A mixture of (S)-6-((1-amino-1-oxopropan-2-yl)amino)-2-(2-fluoropyridin-4-yl)pyrimidine-4-carboxamide (60 mg, 0.2 mmol), 4-fluorophenol (40 mg, 0.2 mmol) and Cs2CO3 (76 mg, 0.2 mmol) in DMF (1 mL) was placed in a microwave reaction vial and heated in a microwave oven at 160° C. for 20 minutes. The reaction was worked up with DCM then dried and evaporated. The residue was subjected to C18 flash chromatography using acetonitrile/H2O/0.1 TFA as the eluent and neutralized to give (S)-6-((1-amino-1-oxopropan-2-yl)amino)-2-(2-(4-fluorophenoxy)pyridin-4-yl)pyrimidine-4-carboxamide as white solid (40 mg, yield 50%). 1H NMR (CD3OD): 7.90-8.21 (3H, m), 6.90-7.2 (5H, m), 4.4 (1H, m), 1.35 (3H, d, J=7.0 Hz). LC/MS: m/z=398 [M+H]+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09163008B2 |
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| Source dataset | uspto-grants-2015_10 |
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| ORD ID | ord-e47e15f34bb443d38e272627c34a9d16 |
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| Source note | uspto-grants-2015_10 |
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