HuagongsheHuagongshe Chemistry Print Report · For research reference only
Water → HCID 58459927, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Dichloromethane | HCID 6344 | — |
| Reactant | Cyclopropylamine | HCID 69828 | — |
| Reactant | 2,4-Dichloro-5-(trifluoromethyl)pyrimidine | HCID 2782774 | — |
| Solvent | Methanol | HCID 887 | — |
| Product | HCID 58459927 | HCID 58459927 | 34.2% |
Reaction Steps
To 2,4-dichloro-5-(trifluoromethyl)pyrimidine (1.25 g, 5.8 mmol) in methanol (4 mL) at 0° C. was added cyclopropylamine (0.69 mL, 10 mmol). The mixture was allowed to stir at RT for 4 h. and then DCM (20 mL) and water (20 mL) were added. The mixture was passed through a hydrophobic frit and the solvent was removed in vacuo. Purification of the residue via silica gel column chromatography (0-100% DCM in iso-hexane) gave 2-chloro-N-cyclopropyl-5-(trifluoromethyl)pyrimidin-4-amine (472 mg, 34%) as an off-white solid. LCMS (10 cm_ESCI_Bicarb_MeCN): [M+H]+=238 at 3.64 min. 1H NMR (400 MHz, CDCl3): δ 8.27 (d, J=1.1 Hz, 1H), 5.56 (br s, 1H), 3.03-2.93 (m, 1H), 0.99-0.89 (m, 2H), 0.65-0.60 (m, 2H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08809331B2 |
| Source dataset | uspto-grants-2014_08 |
| ORD ID | ord-e3242a78d8c14a4e9795208936d75502 |
| Source note | uspto-grants-2014_08 |