Potassium Carbonate → 4-[4-(4-Tetrazol-2-yl-phenoxy)-pyrazolo[3,4-d]pyrimidin-1-yl]-piperidine-1-carboxylic acid tert-butyl ester

HRID 1931688Notes

Reaction equation

HRID 1931688 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([N:14]2[C:18]3=[N:19][CH:20]=[N:21][C:22](Cl)=[C:17]3[CH:16]=[N:15]2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[N:24]1[N:25]([C:29]2[CH:34]=[CH:33][C:32]([OH:35])=[CH:31][CH:30]=2)[N:26]=[N:27][CH:28]=1.C(=O)([O-])[O-].[K+].[K+]>>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([N:14]2[C:18]3=[N:19][CH:20]=[N:21][C:22]([O:35][C:32]4[CH:31]=[CH:30][C:29]([N:25]5[N:26]=[N:27][CH:28]=[N:24]5)=[CH:34][CH:33]=4)=[C:17]3[CH:16]=[N:15]2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 3

HCID 11430Potassium CarbonateHCID 157603994-(2H-Tetrazol-2-yl)phenolHCID 57964905Tert-butyl 4-(4-chloro-1H-pyrazolo[3,4-D]pyrimidin-1-YL)piperidine-1-carboxylate2×

Product 1

HCID 579648824-[4-(4-Tetrazol-2-yl-phenoxy)-pyrazolo[3,4-d]pyrimidin-1-yl]-piperidine-1-carboxylic acid tert-butyl esterYield 19.2%

Procedure

4-[4-(4-Tetrazol-2-yl-phenoxy)-pyrazolo[3,4-d]pyrimidin-1-yl]-piperidine-1-carboxylic acid tert-butyl ester (16 mg, 19%) was prepared using the procedure described for the preparation of Example 41 by the reaction of 4-(4-chloro-pyrazolo[3,4-d]pyrimidin-1-yl)-piperidine-1-carboxylic acid tert-butyl ester (Intermediate 19; 60 mg, 0.18 mmol) with 4-(2H-tetrazol-2-yl)phenol (ChemBridge Corporation, San Diego, Calif., USA; 29 mg, 0.18 mmol) in the presence of potassium carbonate (54 mg, 0.39 mmol).

Sources & evidence

ORD record
ord-be377fe12bea4fdbab2f98d3add3e2ac
Source dataset
uspto-grants-2012_05
Patent number
US08188098B2

Reaction notes

Loading…