1,10-Phenanthroline → 3-(3-Oxo-4-pyrimidin-2-yl-piperazin-1-yl)-azetidine-1-carboxylic acid tert-butyl ester

HRID 473595

Reaktionsgleichung

Reaktionsgleichung von HRID 473595
[C:1]([O:5][C:6]([N:8]1[CH2:11][CH:10]([N:12]2[CH2:17][CH2:16][NH:15][C:14](=[O:18])[CH2:13]2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Br[C:20]1[N:25]=[CH:24][CH:23]=[CH:22][N:21]=1.N1C2C(=CC=C3C=2N=CC=C3)C=CC=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>C1(C)C=CC=CC=1.C(Cl)Cl.[Cu]I>[C:1]([O:5][C:6]([N:8]1[CH2:11][CH:10]([N:12]2[CH2:17][CH2:16][N:15]([C:20]3[N:25]=[CH:24][CH:23]=[CH:22][N:21]=3)[C:14](=[O:18])[CH2:13]2)[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Komponenten

8

Edukt 4

HCID 13181,10-PhenanthrolineHCID 62657Potassium Phosphate, TribasicHCID 783452-BromopyrimidineHCID 596054391-Boc-3-(3-oxo-1-piperazinyl)azetidine

Produkt 1

HCID 668362493-(3-Oxo-4-pyrimidin-2-yl-piperazin-1-yl)-azetidine-1-carboxylic acid tert-butyl esterAusbeute 36,8 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 1140TolueneLösungsmittelHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

A mixture of intermediate 4b (52 mg, 0.204 mmol), 2-bromopyrimidine 1i (65 mg, 0.41 mmol), CuI (8 mg, 0.04 mmol), 1,10-phenanthroline (18 mg, 0.10 mmol), and K3PO4 (95 mg, 0.45 mmol) in toluene (1 mL) was heated at 110° C. under N2 for 9 h. The reaction mixture was diluted with CH2Cl2 and filtered. The solution was concentrated and purification by column chromatography (silica gel, 3% MeOH/CH2Cl2) gave intermediate 3c as light yellow solid (25 mg).

Aufarbeitung

  1. filtrationfiltered
  2. concentrationThe solution was concentrated
  3. custompurification by column chromatography (silica gel, 3% MeOH/CH2Cl2)

Quellen und Nachweise

ORD-Eintrag
ord-68440521ea3d43a188786ef8be7d78a5
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08637498B2

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