Potassium Carbonate → HCID 86636109, compound

HRID 1931731Notes

Reaction equation

[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1)(=[O:4])=[O:3].Cl[C:13]1[N:18]=[CH:17][N:16]=[C:15]2[N:19]([CH:22]3[CH2:27][CH2:26][N:25]([C:28]4[O:32][N:31]=[C:30]([CH:33]([CH3:35])[CH3:34])[N:29]=4)[CH2:24][CH2:23]3)[N:20]=[CH:21][C:14]=12.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([O:11][C:21]2[C:14]3[C:15](=[N:16][CH:17]=[N:18][CH:13]=3)[N:19]([CH:22]3[CH2:23][CH2:24][N:25]([C:28]4[O:32][N:31]=[C:30]([CH:33]([CH3:35])[CH3:34])[N:29]=4)[CH2:26][CH2:27]3)[N:20]=2)=[CH:7][CH:6]=1)(=[O:3])=[O:4]

Participants

Conditions

Temperature: 180 °C

Procedure

A mixture of 4-methanesulfonyl-phenol (available from Acros Organics, Geel, Belgium; 24 mg, 0.14 mmol), 4-chloro-1-[1-(3-isopropyl-[1,2,4]oxadiazol-5-yl)-piperidin-4-yl]-1H-pyrazolo[3,4-d]pyrimidine (Intermediate 22; 40 mg, 0.11 mmol) and potassium carbonate (19 mg, 0.14 mmol) in anhydrous DMF (2 mL) was heated in a Biotage Optimizer microwave at 180° C. for 10 min. The mixture was cooled and filtered through Celite, concentrated and held under vacuum. The residue was purified by flash column chromatography eluting with 0-3% methanol/dichloromethane to give 4-(4-methanesulfonyl-phenoxy-1-[1-(3-isopropyl-[1,2,4]oxadiazol-5-yl)-piperidin-4-yl]-1H-pyrazolo[3,4-d]pyrimidine (40 mg, 72%). Mass spectrum (ES) MH+=483.5.

Workup

temperatureThe mixture was cooled
filtrationfiltered through Celite
concentrationconcentrated
customThe residue was purified by flash column chromatography
washeluting with 0-3% methanol/dichloromethane

Sources & evidence

ORD record: ord-5624edace2e645259b758657428709fe
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08188098B2

Reaction notes

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