Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | 4-Chloro-6-(trifluoromethyl)pyrimidin-2-amine | HCID 13086907 | — |
| Reactant | N-(4-Hydroxymethylbenzyl)trifluoroacetamide | HCID 15852209 | — |
| Solvent | Dimethylacetamide | HCID 31374 | — |
| Product | HCID 86632762 | HCID 86632762 | — |
Reaction Steps
322 mg (1.38 mmol) 2,2,2-trifluoro-N-(4-hydroxymethyl-benzyl)-acetamide is dissolved in 2 mL dry dimethylacetamide under argon atmosphere, and 50 mg (2.1 mmol) NaH is added. 136 mg (0.69 mmol) 4-chloro-6-(trifluoromethyl)pyrimidin-2-amine 24 is then added and the solution stirred at 90° C. over night. 1 mL water is added carefully to quench all excess NaH and the mixture poured into 50 mL 0.5 N HCl. The crude product is extracted with ethyl acetate, the combined organic phases washed with brine and dried over MgSO4. After evaporation of the solvent, the product is purified by flash column chromatography (gradient ethyl acetate: cyclohexane from 1:1 to 3:1).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08178314B2 |
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| Source dataset | uspto-grants-2012_05 |
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| ORD ID | ord-b788a053bc6c4e4987491877be128f08 |
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| Source note | uspto-grants-2012_05 |
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