Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium Sulfate | HCID 24436 | — |
| Reactant | 2-Methylpyrimidin-4-amine | HCID 295763 | — |
| Reactant | Trimethylaluminum | HCID 16682925 | — |
| Reactant | HCID 68406634 | HCID 68406634 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | HCID 68405926 | HCID 68405926 | 63% |
Reaction Steps
A solution of 2-methyl-4-amino-pyrimidine (0.184 g, 1.68 mmol) in 10 ml dry dioxane was treated at 0° C. with trimethylaluminium (2M in hexane, 0.84 ml, 1.68 mmol). The mixture was stirred at room temperature for 1 h. 5-(Cyclopropylmethoxycarbonyl-(cyclopropylmethyl)-amino)-2-methyl-thiazole-4-carboxylic acid ethyl ester (0.135 g, 0.40 mmol) was added and the reaction mixture was refluxed for 4 h. 1 ml water and 2 g sodium sulfate were sequentially added and filtered. The filtrate was evaporated and the residue purified by flash chromatography with heptane/ethyl acetate 100:0→0:100 gradient to yield cyclopropylmethyl-[2-methyl-4-(2-methyl-pyrimidin-4-ylcarbamoyl)-thiazol-5-yl]-carbamic acid cyclopropylmethyl ester (0.101 g, 63%) as a colourless oil, MS (ISP): m/e=402.5 (M+H+).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US07678815B2 |
|---|
| Source dataset | uspto-grants-2010_03 |
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| ORD ID | ord-c4dfdf30bc574ba7afc6e8edad56994c |
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| Source note | uspto-grants-2010_03 |
|---|