Carbonate Ion → HCID 57544435, compound

HRID 1931601Notes

Reaction equation

HRID 1931601 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([N:14]2[C:18]3=[N:19][CH:20]=[N:21][C:22]([O:23][C:24]4[C:25]([CH3:30])=[N:26][CH:27]=[CH:28][CH:29]=4)=[C:17]3[CH:16]=[N:15]2)[CH2:10][CH2:9]1)=O)(C)(C)C.C(=O)([O-])[O-]>FC(F)(F)C(O)=O.ClCCl>[CH3:30][C:25]1[C:24]([O:23][C:22]2[N:21]=[CH:20][N:19]=[C:18]3[N:14]([CH:11]4[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]4)[N:15]=[CH:16][C:17]=23)=[CH:29][CH:28]=[CH:27][N:26]=1

Participants

4

Reactant 2

HCID 19660Carbonate IonHCID 44622155HCID 44622155, compound

Product 1

HCID 57544435HCID 57544435, compoundYield 68.8%

Reagents, catalysts & solvents 1

HCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

A solution of 4-[4-(2-methyl-pyridin-3-yloxy)-pyrazolo[3,4-d]pyrimidin-1-yl]-piperidine-1-carboxylic acid tert-butyl ester (Example 92; 710 mg, 1.7 mmol) in 20% trifluoroacetic acid/dichloromethane (15 mL) was stirred at room temperature for 40 min, then the solvents were evaporated and the residue held under high vacuum to give a pale yellow thick oil. SiliaBond Carbonate (Silicycle, Quebec City, Canada; 4 equivalents) was added and the mixture was stirred slowly for 2.5 h, then filtered. The filtrate was evaporated and held under high vacuum to give 4-(2-methyl-pyridin-3-yloxy)-1-piperidin-4-yl-1H-pyrazolo[3,4-d]pyrimidine (363 mg, 68%) as a white solid.

Workup

  1. customthe solvents were evaporated
  2. customto give a pale yellow thick oil
  3. filtrationfiltered
  4. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-9fc0d59a26554b2db0607bfdeb2d8c8d
Source dataset
uspto-grants-2012_05
Patent number
US08188098B2

Reaction notes

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