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

HRID 1931686Notes

Reaction equation

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

Participants

Conditions

Temperature: 180 °C

Procedure

A mixture of 4-(1,2,4)-triazol-1-yl-phenol (Lancaster; 14 mg, 0.09 mmol), 4-(4-chloro-pyrazolo[3,4-d]pyrimidin-1-yl)-piperidine-1-carboxylic acid tert-butyl ester (Intermediate 19; 29.5 mg, 0.09 mmol) and potassium carbonate (14.4 mg, 0.10 mmol) in anhydrous DMF (1 mL) was heated in a microwave at 180° C. for 10 min. The mixture was cooled and filtered. The solid was washed with dichloromethane. The filtrate was concentrated and purified using a 4 g silica gel column, eluting with 0-5% methanol/dichloromethane to give 4-[4-(4-[1,2,4]triazol-1-yl-phenoxy)-pyrazolo[3,4-d]pyrimidin-1-yl]-piperidine-1-carboxylic acid tert-butyl ester (17 mg, 42%).

Workup

temperatureThe mixture was cooled
filtrationfiltered
washThe solid was washed with dichloromethane
concentrationThe filtrate was concentrated
custompurified
washeluting with 0-5% methanol/dichloromethane

Sources & evidence

ORD record: ord-2083c48bac7b4ee094522fe1376e1d39
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08188098B2

Reaction notes

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