Triethylamine → 1,1-Dimethylethyl 4-(4-(5-chloro-2-hydroxyphenyl)-2-pyrimidinyl)-1-piperazinecarboxylate

HRID 2283621Notes

Reaction equation

HRID 2283621 reaction equation
[N:1]1([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[Cl:14][C:15]1[CH:20]=[CH:19][C:18]([OH:21])=[C:17]([C:22]2[CH:27]=[CH:26][N:25]=[C:24](Cl)[N:23]=2)[CH:16]=1.C(N(CC)CC)C>C(O)(C)C.C(OCC)(=O)C>[Cl:14][C:15]1[CH:20]=[CH:19][C:18]([OH:21])=[C:17]([C:22]2[CH:27]=[CH:26][N:25]=[C:24]([N:4]3[CH2:5][CH2:6][N:1]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:2][CH2:3]3)[N:23]=2)[CH:16]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 143452tert-Butyl piperazine-1-carboxylateHCID 135743684HCID 135743684, compound

Product 1

HCID 1357436831,1-Dimethylethyl 4-(4-(5-chloro-2-hydroxyphenyl)-2-pyrimidinyl)-1-piperazinecarboxylate

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

tert-Butyl piperazine-1-carboxylate (24.0 mg, 0.13 mmol) was added to a mixture of 4-chloro-2-(2-chloropyrimidin-4-yl)phenol (Preparation 1, 30.1 mg, 0.13 mmol), and triethylamine (61.2 uL, 0.44 mmol) in isopropyl alcohol (0.2 mL). The reaction mixture was stirred at ambient temperature. After 18 hours, LCMS analysis indicated the reaction was not complete. The reaction mixture was heated for 30 minutes at 70° C. then cooled to ambient temperature. The reaction mixture was diluted with ethyl acetate, washed with water then brine, dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo to afford the title compound as a light brown paste (50 mg).

Workup

  1. temperatureThe reaction mixture was heated for 30 minutes at 70° C.
  2. temperaturethen cooled to ambient temperature
  3. washwashed with water
  4. dry with materialbrine, dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-241e0f3669494f968897fa6a3c1781e9
Source dataset
uspto-grants-2015_09
Patent number
US09145407B2

Reaction notes

Loading…