Methanesulfonic Acid → HCID 58456162, compound

HRID 595150Notes

Reaction equation

CS(O)(=O)=O.Cl[C:7]1[N:12]=[C:11]([O:13][CH3:14])[C:10]([F:15])=[CH:9][N:8]=1.[CH3:16][C:17]1[CH:18]=[C:19]([CH:21]=[C:22]([B:24]2[O:28][C:27]([CH3:30])([CH3:29])[C:26]([CH3:32])([CH3:31])[O:25]2)[CH:23]=1)[NH2:20]>O1CCOCC1.CCOC(C)=O>[F:15][C:10]1[C:11]([O:13][CH3:14])=[N:12][C:7]([NH:20][C:19]2[CH:21]=[C:22]([B:24]3[O:28][C:27]([CH3:29])([CH3:30])[C:26]([CH3:32])([CH3:31])[O:25]3)[CH:23]=[C:17]([CH3:16])[CH:18]=2)=[N:8][CH:9]=1

Participants

Conditions

Temperature: 100 °C

Procedure

Methanesulfonic acid (0.13 mL, 1.97 mmol) was added to a solution of 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) in dioxane (17 mL). The reaction mixture was heated at 100° C. overnight. The reaction was then cooled to room temperature, diluted with EtOAc, washed with water, dried over magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel to afford 5-fluoro-4-methoxy-N-[3-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-pyrimidin-2-amine MS ESI calc'd for C18H24BFN3O3 [M+H]+ 360. found 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 under reduced pressure
customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record: ord-4fcf06b8a0cf4edb9c4ccdee18391efb
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09242984B2

Reaction notes

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