Methanesulfonic Acid → HCID 58456197, compound

HRID 410400Notes

Reaction equation

Cl[C:2]1[N:7]=[C:6]([O:8][CH2:9][CH2:10][CH2:11][O:12][CH3:13])[CH:5]=[CH:4][N:3]=1.[CH3:14][C:15]1[CH:16]=[C:17]([CH:19]=[C:20]([B:22]2[O:26][C:25]([CH3:28])([CH3:27])[C:24]([CH3:30])([CH3:29])[O:23]2)[CH:21]=1)[NH2:18].CS(O)(=O)=O>O1CCOCC1>[CH3:13][O:12][CH2:11][CH2:10][CH2:9][O:8][C:6]1[CH:5]=[CH:4][N:3]=[C:2]([NH:18][C:17]2[CH:19]=[C:20]([B:22]3[O:26][C:25]([CH3:27])([CH3:28])[C:24]([CH3:30])([CH3:29])[O:23]3)[CH:21]=[C:15]([CH3:14])[CH:16]=2)[N:7]=1

Participants

Conditions

Temperature: 100 °C

Procedure

The product of Step 1 (107 mg, 0.528 mmol) and 3-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (123 mg, 0.528 mmol) were dissolved in Dioxane (4 ml), and methanesulfonic acid (0.036 ml, 0.554 mmol) was added. The mixture was heated to 100° C. for 18 h. The mixture was allowed to cool to room temperature, quenched with saturated aqueous sodium bicarbonate and extracted with EtOAc (2×). The combined organic layers were dried over Na2SO4 and concentrated in vacuo to afford 4-(3-methoxypropoxy)-N-[3-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]pyrimidin-2-amine (165 mg, 78%) as a brown solid. MS ESI: [M+H]+ m/z 400. 1H NMR (500 MHz, CDCl3) δ 8.09 (d, J=5.8, 1H), 7.82 (s, 1H), 7.59 (s, 1H), 7.32 (s, 1H), 6.17 (d, J=4.4, 1H), 4.48 (t, J=5.8, 2H), 3.53 (t, J=5.5, 2H), 3.34 (s, 3H), 2.37 (s, 3H), 2.05 (dd, J=3.3, 9.4, 2H), 1.34 (s, 12H).

Workup

temperatureto cool to room temperature
customquenched with saturated aqueous sodium bicarbonate
extractionextracted with EtOAc (2×)
dry with materialThe combined organic layers were dried over Na2SO4
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-efa2557461a14b8f805c63dd415967dc
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08759366B2

Reaction notes

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