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Potassium Carbonate → HCID 57964968, compound

HRID 1931734
Notes
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Reaction equation

HRID 1931734 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 11430Potassium Carbonate2×HCID 707192-Methylpyridin-3-olHCID 579649944-chloro-1-[1-(3-isopropyl-[1,2,4]oxadiazol-5-yl)-piperidin-4-yl]-1H-pyrazolo[3,4-d]pyrimidine2×

Product 1

HCID 57964968HCID 57964968, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent
2×

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

  1. customno reaction
  2. temperaturethe reaction mixture was heated in a microwave at 180° C. for 15 min
  3. customThe solvent was evaporated
  4. additionwater was added
  5. extractionThe mixture was extracted with ethyl acetate
  6. customthe extracts were dried
  7. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes