Water → 4-[2-(3-Chloro-benzylamino)-pyrimidin-4-yl]-piperazine-1-carboxylic acid tert-butyl ester

HRID 890568Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 890568
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][N:17]=[C:16](Cl)[N:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Cl:21][C:22]1[CH:23]=[C:24]([CH:27]=[CH:28][CH:29]=1)[CH2:25][NH2:26].C(=O)([O-])[O-].[K+].[K+].O>C(O)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][N:17]=[C:16]([NH:26][CH2:25][C:24]3[CH:27]=[CH:28][CH:29]=[C:22]([Cl:21])[CH:23]=3)[N:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Komponenten

6

Edukt 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 77802Benzenemethanamine, 3-chloro-HCID 11197306Tert-butyl 4-(2-chloropyrimidin-4-yl)piperazine-1-carboxylate

Produkt 1

HCID 695961184-[2-(3-Chloro-benzylamino)-pyrimidin-4-yl]-piperazine-1-carboxylic acid tert-butyl esterAusbeute 36,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of 4-(2-chloro-pyrimidin-4-yl)-piperazine-1-carboxylic acid tert-butyl ester (100 mg, 0.33 mmol), 3-chlorobenzylamine (0.65 mL, 5.3 mmol) and potassium carbonate (71 mg, 0.67 mmol) in ethanol (5 mL) was heated at reflux for 7 days. The reaction mixture was cooled to room temperature, poured into H2O (15 mL) and extracted with EtOAc (2×20 mL). The combined organic extracts were washed with H2O (3×15 mL), brine, dried (Na2SO4) and concentrated in vacuo. The residue was purified by preparative TLC (10% MeOH in CH2Cl2) to give a yellow solid. The yellow solid was triturated with MeOH (1 mL) and the solid was collected by filtration to give intermediate (I-3a) as a white solid (48.5 mg).

Aufarbeitung

  1. temperaturewas heated
  2. temperatureat reflux for 7 days
  3. extractionextracted with EtOAc (2×20 mL)
  4. washThe combined organic extracts were washed with H2O (3×15 mL), brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by preparative TLC (10% MeOH in CH2Cl2)
  8. customto give a yellow solid
  9. customThe yellow solid was triturated with MeOH (1 mL)
  10. filtrationthe solid was collected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-f691f4c9e1244752bd15526c0fdd6c9f
Quelldatensatz
uspto-grants-2006_02
Patentnummer
US06995159B2

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