Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Tert-Butylamine | HCID 6385 | — |
| Reactant | 4-Chloro-2-(methylthio)pyrimidine-5-carboxylic acid ethyl ester | HCID 80008 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Solvent | Ethanol | HCID 702 | — |
| Product | HCID 295702 | HCID 295702 | 92% |
Reaction Steps
A mixture of ethyl 4-chloro-2-(methylthio)pyrimidine-5-carboxylate (3 g, 12.89 mmol), 2-methylpropan-2-amine (1.565 mL, 14.83 mmol) and DIEA (2.93 mL, 16.76 mmol) in ethanol (20 mL) was heated at 60° C. overnight. After cooling to room temperature, the solvent was concentrated under reduced pressure and water was added. The aqueous phase was extracted three times with ethyl acetate and the combined organic phases were dried over anhydrous magnesium sulfate, filtered and evaporated to give ethyl 4-(tert-butylamino)-2-(methylthio)pyrimidine-5-carboxylate (3.20 g, 11.86 mmol, 92% yield) as a colorless oil. MS (ESI) m/z. 269.5 [M+1]+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09139534B2 |
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| Source dataset | uspto-grants-2015_09 |
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| ORD ID | ord-9261017d598145909609e41feb9161a2 |
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| Source note | uspto-grants-2015_09 |
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