Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Furfurylamine | HCID 3438 | — |
| Reactant | 4-Chloro-2-(methylthio)pyrimidine-5-carboxylic acid ethyl ester | HCID 80008 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Solvent | Isopropanol | HCID 3776 | — |
| Product | HCID 28905833 | HCID 28905833 | 89.8% |
Reaction Steps
To a solution of ethyl 4-chloro-2-(methylthio)pyrimidine-5-carboxylate (1.71 g) in 2-propanol (10 ml) were added furfurylamine (714 mg) and diisopropylethylamine (950 mg), and the mixture was stirred at room temperature for 10 min. The reaction mixture was poured into 2% aqueous sodium hydrogen carbonate, and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. Ethyl acetate was added to the residue, and the precipitate was collected by filtration. The precipitate was dissolved in ethanol (10 ml), 2 M aqueous sodium hydroxide solution (10 ml) was added and the mixture was stirred at room temperature for 5 hr. The reaction mixture was adjusted to pH 3 with 1 M hydrochloric acid, and the precipitated crystals were collected by filtration to give the object compound (1.75 g) as a powder.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08329691B2 |
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| Source dataset | uspto-grants-2012_12 |
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| ORD ID | ord-9f2a77065a3e4b48af5d1b5eb6961ab3 |
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| Source note | uspto-grants-2012_12 |
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