Trifluoroacetic acid → HCID 21477622, compound

HRID 2395750Notes

Reaction equation

HRID 2395750 reaction equation
FC(F)(F)C(O)=O.CC(C)(OC([N:14]1[CH2:19][CH2:18][N:17]([C:20]2[C:25]([NH:26][CH:27]([CH3:29])[CH3:28])=[CH:24][N:23]=[CH:22][N:21]=2)[CH2:16][CH2:15]1)=O)C>ClCCl.[OH-].[Na+]>[CH3:29][CH:27]([NH:26][C:25]1[C:20]([N:17]2[CH2:16][CH2:15][NH:14][CH2:19][CH2:18]2)=[N:21][CH:22]=[N:23][CH:24]=1)[CH3:28]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 214776211,1-Dimethylethyl 4-[5-[(1-methylethyl)amino]-4-pyrimidinyl]-1-piperazinecarboxylate

Product 1

HCID 21477622HCID 21477622, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 14798Sodium HydroxideSolvent

Procedure

Trifluoroacetic acid (5 ml) is added to a solution of 1-[1,1-dimethylethoxy-carbonyl]-4-[5-(1-methylethylamino)-4-pyrimidinyl]piperazine (PREPARATION 29, 0.37 g) in dichloromethane (20 ml) at - 78°. The reaction is allowed to warm to 20°-25° overnight, and then diluted with excess aqueous sodium hydroxide solution (10%). The phases are separated. The aqueous phase is extracted twice again with dichloromethane. The combined organic extracts are washed with saline, dried over sodium sulfate, and concentrated under reduced pressure to give the title compound, NMR (CDCl3) 1.25, 1.7, 3.01, 3.21, 3.45, 3.5, 7.86 and 8.34 δ.

Workup

  1. temperatureto warm to 20°-25° overnight
  2. customThe phases are separated
  3. extractionThe aqueous phase is extracted twice again with dichloromethane
  4. washThe combined organic extracts are washed with saline
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-8237cfe1d48c48b19da6061911b8a8b1
Source dataset
uspto-grants-1996_02
Patent number
US05489593

Reaction notes

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