Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Water | HCID 962 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | HCID 19392528 | HCID 19392528 | — |
| Reactant | HCID 178418573 | HCID 178418573 | — |
| Solvent | Diethyl Ether | HCID 3283 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 19392516 | HCID 19392516 | 88% |
Reaction Steps
Methyl magnesium bromide (115 ml of a 3.0M solution in ether) was added to 2-cyano-4-(2,2,2-trifluoroethoxy)-pyrimidine (70.0 g) in THF (300 ml) at -40° C. After the addition it was stirred for 11/2 hours at -40° C. then treated with water (50 ml), followed by enough 2M hydrochloric acid to make the reaction mixture just acid, this was stirred for 11/2 hours and then neutralised with sodium bicarbonate, and extracted with ether (3×300 ml). The combined ether extracts were dried and concentrated to give 2-acetyl-4-(2,2,2-trifluoroethoxy)-pyrimidine (66.8 g, 88% yield) as a brown oil; IR maxima (film): 1718 cm-1 ; 1H NMR (270 MHz): δ2.74(3H,s), 4.92(2H,q), 7.05(1H,d), 8.74(1H,d) ppm.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US05439910 |
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| Source dataset | uspto-grants-1995_08 |
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| ORD ID | ord-a14c55e52a994b339553a5cb8be1b3c6 |
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| Source note | uspto-grants-1995_08 |
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