Methanesulfonic Acid → HCID 58456162, compound

HRID 410396Notes

Reaction equation

Cl[C:2]1[N:7]=[C:6]([O:8][CH3:9])[C:5]([F:10])=[CH:4][N:3]=1.[CH3:11][C:12]1[CH:13]=[C:14]([CH:16]=[C:17]([B:19]2[O:23][C:22]([CH3:25])([CH3:24])[C:21]([CH3:27])([CH3:26])[O:20]2)[CH:18]=1)[NH2:15].O1CCOCC1.CS(O)(=O)=O>C(OCC)(=O)C>[F:10][C:5]1[C:6]([O:8][CH3:9])=[N:7][C:2]([NH:15][C:14]2[CH:16]=[C:17]([B:19]3[O:23][C:22]([CH3:24])([CH3:25])[C:21]([CH3:27])([CH3:26])[O:20]3)[CH:18]=[C:12]([CH3:11])[CH:13]=2)=[N:3][CH:4]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a flask containing 2-chloro-5-fluoro-4-methoxypyrimidine (0.32 g, 1.97 mmol) and 3-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (0.40 g, 1.72 mmol) were added dioxane (17 mL) and methanesulfonic acid (0.13 mL, 1.97 mmol). The reaction was heated at 100° C. overnight. The reaction was then cooled to room temperature, diluted with ethyl acetate, washed with water, dried over magnesium sulfate, filtered and concentrated. Flash chromatography was used for purification to yield 5-fluoro-4-methoxy-N-[3-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]pyrimidin-2-amine (0.31 g, 0.86 mmol, 50% yield). MS ESI: [M+H]+ m/z 360. 1H NMR (500 MHz, DMSO-d6) δ 9.51 (s, 1H), 8.27 (d, J=3.2, 1H), 8.00 (s, 1H), 7.57 (s, 1H), 7.07 (s, 1H), 4.01 (s, 3H), 2.25 (s, 3H), 1.26 (s, 12H).

Workup

temperatureThe reaction was then cooled to room temperature
washwashed with water
dry with materialdried over magnesium sulfate
filtrationfiltered
concentrationconcentrated
customFlash chromatography was used for purification

Sources & evidence

ORD record: ord-27609a27f5c24f1fa34bcb5904b5e891
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08759366B2

Reaction notes

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