Potassium Carbonate → HCID 57964968, compound

HRID 1931734Notes

Reaction equation

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

Participants

Conditions

Temperature: 160 °C

Procedure

A mixture of 3-hydroxy-2-methylpyridine (Aldrich Chemical Company, Inc., Milwaukee, Wis., USA; 1.25 mg, 0.011 mmol), 4-chloro-1-[1-(3-isopropyl-[1,2,4]oxadiazol-5-yl)-piperidin-4-yl]-1H-pyrazolo[3,4-d]pyrimidine (Intermediate 22; 4 mg, 0.012 mmol) and potassium carbonate (3 mg, 0.022 mmol) in DMF (0.5 mL) was heated in a microwave at 160° C. for 10 min, but TLC showed no reaction. Potassium carbonate (3 mg, 0.022 mmol) and DMF (0.1 mL) were added and the reaction mixture was heated in a microwave at 180° C. for 15 min. The solvent was evaporated and water was added. The mixture was extracted with ethyl acetate and the extracts were dried, held under high vacuum, and purified by HPLC to give 1-[1-(3-Isopropyl-[1,2,4]oxadiazol-5-yl)-piperidin-4-yl]-4-(2-methyl-pyridin-3-yloxy)-1H-pyrazolo[3,4-d]pyrimidine (1.8 mg, 39%).

Workup

customno reaction
temperaturethe reaction mixture was heated in a microwave at 180° C. for 15 min
customThe solvent was evaporated
additionwater was added
extractionThe mixture was extracted with ethyl acetate
customthe extracts were dried
custompurified by HPLC

Sources & evidence

ORD record: ord-40417ca996f3432f879035b2c5550a93
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08188098B2

Reaction notes

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