Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | 4-Chloro-6-(trifluoromethyl)pyrimidine | HCID 11542881 | — |
| Reactant | (S)-Tert-butyl 2-(4-aminophenyl)morpholine-4-carboxylate | HCID 66705988 | — |
| Solvent | Dimethylacetamide | HCID 31374 | — |
| Product | HCID 86671414 | HCID 86671414 | 89% |
Reaction Steps
A mixture of (5)-tert-butyl 2-(4-aminophenyl)morpholine-4-carboxylate (100 mg, 0.36 mmol), 4-chloro-6-(trifluoromethyl)pyrimidine (72 mg, 0.4 mmol) and diisopropylethylamine (70 mg, 0.54 mmol) was dissolved in dimethylacetamide (1.3 ml) and stirred at 80° C. overnight. For work-up water was added, and the mixture was extracted with ethyl acetate twice. The combined organic layers were dried (MgSO4) and concentrated in vacuo. The residue was purified by flash chromatography (10 g silica gel, 20 to 40% ethyl acetate in heptane) to yield a white solid (135 mg, 89%). MS (ISP): 425.2 ([M+H]+).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08802673B2 |
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| Source dataset | uspto-grants-2014_08 |
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| ORD ID | ord-fe5412c0e2cc4afb8e47d54dfbd74fd2 |
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| Source note | uspto-grants-2014_08 |
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