Trifluoroacetic acid → 2-[6-(4-Chloro-benzyl)-2-(piperidin-4-ylamino)-pyrimidin-4-yl]-propan-2-ol

HRID 451421Notes

Reaction equation

HRID 451421 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]2[N:20]=[C:19]([CH2:21][C:22]3[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=3)[CH:18]=[C:17]([C:29]([OH:32])([CH3:31])[CH3:30])[N:16]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O.C(=O)([O-])[O-].[Na+].[Na+]>ClCCl>[Cl:28][C:25]1[CH:24]=[CH:23][C:22]([CH2:21][C:19]2[N:20]=[C:15]([NH:14][CH:11]3[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]3)[N:16]=[C:17]([C:29]([OH:32])([CH3:31])[CH3:30])[CH:18]=2)=[CH:27][CH:26]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 10340Sodium CarbonateHCID 673420264-[4-(4-Chloro-benzyl)-6-(1-hydroxy-1-methyl-ethyl)-pyrimidin-2-ylamino]-piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 673418332-[6-(4-Chloro-benzyl)-2-(piperidin-4-ylamino)-pyrimidin-4-yl]-propan-2-olYield 119%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-[4-(4-chloro-benzyl)-6-(1-hydroxy-1-methyl-ethyl)-pyrimidin-2-ylamino]-piperidine-1-carboxylic acid tert-butyl ester (220 mg, 0.447 mmol) in dichloromethane (5 mL) was added at 0° C. trifluoroacetic acid (365 μL, 4.77 mmol) and the mixture was stirred for 18 hours while allowing to warm to ambient temperature. It was basified by addition of 1 M aqueous sodium carbonate solution (5 mL) and extracted with dichloromethane (15 mL). The organic layers were washed with 1 M aqueous sodium carbonate solution (15 mL) and dried over sodium sulfate. Concentration afforded the title compound (192 mg, 99%) as a brown semi-solid.

Workup

  1. extractionextracted with dichloromethane (15 mL)
  2. washThe organic layers were washed with 1 M aqueous sodium carbonate solution (15 mL)
  3. dry with materialdried over sodium sulfate
  4. concentrationConcentration

Sources & evidence

ORD record
ord-763f30b5d33b4910824d52da657a436f
Source dataset
uspto-grants-2013_07
Patent number
US08486967B2

Reaction notes

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