Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | tert-Butyl ((5-methyl-1,3,4-thiadiazol-2-yl)methyl)(2-methyl-6-(((1S,2S)-2-(5-methylpyridin-2-yl)cyclopropyl)methoxy)pyrimidin-4-yl)carbamate | HCID 86729565 | — |
| Solvent | Methanol | HCID 887 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | MK-8189 | HCID 71271414 | 72% |
Reaction Steps
To a solution of 2-2 (51.0 mg, 0.11 mmol) in MeOH (0.53 mL) was added K2CO3 (17.5 mg, 0.13 mmol). The resulted suspension was stirred at 70° C. for 2 hour. The mixture was diluted with EtOAc, and then extracted with 1N HCl. The aqueous layer was basified with 5N NaOH and extracted with DCM three times. The combined DCM layers were dried over Na2SO4 and concentrated to give 2-3″ as an off white solid (29 mg, 72%). MS (M+H)+: observed=383.1654, calculated=383.1649. 1H NMR (400 MHz, DMSO-d6): δ 8.22 (s, 1H), 7.82 (br t, J=5.0 Hz, 1H), 7.45 (d, J=7.9 Hz, 1H), 7.17 (d, J=7.7 Hz, 1H), 5.64 (s, 1H), 4.76 (d, J=5.0 Hz, 2H), 4.23 (m, 1H), 4.14 (m, 1H), 2.65 (s, 3H), 2.31 (s, 3H), 2.22 (s, 3H), 2.09 (m, 1H), 1.71 (m, 1H), 1.12 (m, 1H), 0.98 (m, 1H)
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US09062059B2 |
|---|
| Source dataset | uspto-grants-2015_06 |
|---|
| ORD ID | ord-0fc85cc44ec247d1a5acf0d025f95334 |
|---|
| Source note | uspto-grants-2015_06 |
|---|
