Methanesulfonic Acid → N-[3-bromo-5-(methoxymethyl)phenyl]-4-(trifluoromethyl)pyrimidin-2-amine

HRID 1039895Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]([CH:6]=[C:7]([CH2:9][O:10][CH3:11])[CH:8]=1)[NH2:5].Cl[C:13]1[N:18]=[C:17]([C:19]([F:22])([F:21])[F:20])[CH:16]=[CH:15][N:14]=1.CS(O)(=O)=O>O1CCOCC1.C(OCC)(=O)C>[Br:1][C:2]1[CH:3]=[C:4]([NH:5][C:13]2[N:18]=[C:17]([C:19]([F:22])([F:21])[F:20])[CH:16]=[CH:15][N:14]=2)[CH:6]=[C:7]([CH2:9][O:10][CH3:11])[CH:8]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of the product of Step 2 (258 mg, 1.194 mmol) in dioxane (3.8 mL) were added 2-chloro-4-(trifluoromethyl)pyrimidine (251 mg, 1.373 mmol) and methanesulfonic acid (0.07 mL, 1.015 mmol). The reaction was then stirred overnight at 100° C. The reaction was then cooled, diluted with ethyl acetate and then washed with brine solution. The organic layer was collected, dried over magnesium sulfate and then filtered. Ethyl acetate was then removed in vacuo. Flash chromatography (hexane/ethyl acetate: 70/30) was used for purification to afford N-[3-bromo-5-(methoxymethyl)phenyl]-4-(trifluoromethyl)pyrimidin-2-amine as an off-white solid (314 mg, 0.867 mmol, 72.6% yield). MS ESI: [M+H]+ m/z=362.0.

Workup

temperatureThe reaction was then cooled
washwashed with brine solution
customThe organic layer was collected
dry with materialdried over magnesium sulfate
filtrationfiltered
customEthyl acetate was then removed in vacuo
customFlash chromatography (hexane/ethyl acetate: 70/30) was used for purification

Sources & evidence

ORD record: ord-367a37f8663a4074ad58a8dbd10fd62f
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08551984B2

Reaction notes

Loading…