Water → 3-Oxo-4-pyrimidin-2-yl-piperazine-1-carboxylic acid tert-butyl ester

HRID 473592Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 473592
[C:1]([N:8]1[CH2:13][CH2:12][NH:11][C:10](=[O:14])[CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[H-].[Na+].Br[C:18]1[N:23]=[CH:22][CH:21]=[CH:20][N:19]=1.O>CN(C=O)C>[C:4]([O:3][C:1]([N:8]1[CH2:13][CH2:12][N:11]([C:18]2[N:23]=[CH:22][CH:21]=[CH:20][N:19]=2)[C:10](=[O:14])[CH2:9]1)=[O:2])([CH3:7])([CH3:6])[CH3:5]

Komponenten

6

Edukt 4

HCID 962WaterHCID 24758Sodium hydrideHCID 783452-BromopyrimidineHCID 3157178Tert-butyl 3-oxopiperazine-1-carboxylate

Produkt 1

HCID 668236883-Oxo-4-pyrimidin-2-yl-piperazine-1-carboxylic acid tert-butyl esterAusbeute 22,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

To 1-Boc-3-oxopiperazine 3a (390 mg, 1.95 mmol) in DMF (5 mL) at 0° C. was added NaH (60% in oil, 97 mg, 2.44 mmol). The reaction was stirred at 0° C. for 25 min before a solution of 2-bromopyrimidine 1i (465 mg, 2.92 mmol) in DMF (2 mL) was added. The reaction was slowly warmed up to room temperature overnight. To the reaction mixture was added H2O, and the resulting mixture was extracted with EtOAc. The organic solution was washed with aq. NaCl, dried over Na2SO4 and concentrated. Purification by column chromatography (silica gel, 3% MeOH/CH2Cl2) gave 3b as yellow oil (120 mg).

Aufarbeitung

  1. additionwas added
  2. extractionthe resulting mixture was extracted with EtOAc
  3. washThe organic solution was washed with aq. NaCl
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customPurification by column chromatography (silica gel, 3% MeOH/CH2Cl2)

Quellen und Nachweise

ORD-Eintrag
ord-fc838a80b82e4d749e867ac2a3ccc6be
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08637498B2

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