Methyl iodide → HCID 57991935, compound

HRID 2075369Notes

Reaction equation

[CH:1]([C@@H:4]1[C:9]([O:10][CH3:11])=[N:8][C@@H:7]([C@H:12]([C:14]2[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][CH:15]=2)[OH:13])[C:6]([O:24][CH3:25])=[N:5]1)([CH3:3])[CH3:2].[CH2:26]1COCC1.CI.[H-].[Na+]>CCOC(C)=O>[CH:1]([C@@H:4]1[C:9]([O:10][CH3:11])=[N:8][C@@H:7]([C@@H:12]([O:13][CH3:26])[C:14]2[CH:19]=[CH:18][C:17]([C:20]([F:22])([F:21])[F:23])=[CH:16][CH:15]=2)[C:6]([O:24][CH3:25])=[N:5]1)([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 10 °C

Procedure

To a mixture of (S)-((2S,5R)-5-isopropyl-3,6-dimethoxy-2,5-dihydropyrazin-2-yl)(4-(trifluoromethyl)phenyl)methanol (4.09 g, 11.4 mmol) (prepared as shown in Scheme 27) and THF (60 mL) at 0° C., was added methyl iodide (4.28 mL, 68.5 mmol) and sodium hydride (60% dispersion in mineral oil, 0.55 g, 13.7 mmol). The mixture was stirred and gradually warmed to 10° C., then diluted with EtOAc and washed with saturated NH4Cl. The aqueous layer was extracted with EtOAc three times. The combined organic layers were washed with water and brine, dried over Na2SO4 and concentrated in vacuo. The resulting product was purified by chromatography on silica gel (0-10% EtOAc-hexane) to provide the title product as a white solid (3.7 g, 88%). LCMS (API-ES) m/z: 373 (M+H+).

Workup

washwashed with saturated NH4Cl
extractionThe aqueous layer was extracted with EtOAc three times
washThe combined organic layers were washed with water and brine
dry with materialdried over Na2SO4
concentrationconcentrated in vacuo
customThe resulting product was purified by chromatography on silica gel (0-10% EtOAc-hexane)

Sources & evidence

ORD record: ord-7ae8f916ecfe4cf696fbc9e75368de59
Source dataset: uspto-grants-2011_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07919504B2

Reaction notes

Loading…