Potassium Iodide → 5-{3-[1-(4-amino-3-methyl-1H-pyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-5-chloro-2-methoxy-6-methylphenyl}-1,3-oxazolidin-2-one

HRID 1499950Notes

Reaction equation

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

Participants

Conditions

Temperature: 140 °C

Procedure

A mixture of 5-[3-chloro-5-(1-chloroethyl)-6-methoxy-2-methylphenyl]-1,3-oxazolidin-2-one (17 mg, 0.056 mmol) (racemic mixture of two diastereomers from step 3) 3-methyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine (10 mg, 0.067 mmol), cesium carbonate (27 mg, 0.084 mmol) and potassium iodide (0.93 mg, 0.0056 mmol) in N,N-dimethylformamide (0.18 mL) was heated at 140° C. for 1 hour. The mixture was diluted with ether, washed with water, concentrated and purified by preparative LCMS (pH 10) to give the desired compound as a racemic mixture of two diastereomers, 2.2 mg, 9%; LCMS calculated for C19H22ClN6O3 (M+H)+: m/z=417.1; found: 417.1.

Workup

washwashed with water
concentrationconcentrated
custompurified by preparative LCMS (pH 10)

Sources & evidence

ORD record: ord-4048d48927c2443e9de2f28a59422c65
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09199982B2

Reaction notes

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