4,4-Dimethylpiperidine → 5-(3'-Amino-4,4-dimethyl-3,4,5,6-tetrahydro-2H-[1,2']bipyridinyl-6'-yl)-1,3-dimethyl-tetrahydro-pyrimidin-2-one

HRID 408953Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 408953
C(OC(=O)[NH:7][C:8]1[C:9](Br)=[N:10][C:11]([CH:14]2[CH2:19][N:18]([CH3:20])[C:17](=[O:21])[N:16]([CH3:22])[CH2:15]2)=[CH:12][CH:13]=1)(C)(C)C.[CH3:25][C:26]1([CH3:32])[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]1>>[NH2:7][C:8]1[C:9]([N:29]2[CH2:30][CH2:31][C:26]([CH3:32])([CH3:25])[CH2:27][CH2:28]2)=[N:10][C:11]([CH:14]2[CH2:15][N:16]([CH3:22])[C:17](=[O:21])[N:18]([CH3:20])[CH2:19]2)=[CH:12][CH:13]=1

Komponenten

3

Edukt 2

HCID 1381004,4-DimethylpiperidineHCID 59771238[2-Bromo-6-(1,3-dimethyl-2-oxo-hexahydro-pyrimidin-5-yl)-pyridin-3-yl]-carbamic acid tert-butyl ester

Produkt 1

HCID 597712375-(3'-Amino-4,4-dimethyl-3,4,5,6-tetrahydro-2H-[1,2']bipyridinyl-6'-yl)-1,3-dimethyl-tetrahydro-pyrimidin-2-one

Versuchsvorschrift

The title compound is prepared from [2-bromo-6-(1,3-dimethyl-2-oxo-hexahydro-pyrimidin-5-yl)-pyridin-3-yl]-carbamic acid tert-butyl ester (as prepared in the previous step) and 4,4-dimethylpiperidine (US 2003236247) following the literature procedure of Buchwald (Org. Lett., 4, 2885-8 (2002)). The residue obtained is purified by silica gel chromatography with an appropriate solvent mixture. After isolation, removal of the BOC protecting group from the resulting intermediate is carried out by stirring at RT in TFA-DCM (1:2), monitoring by TLC for completion, and then concentration in vacuo.

Aufarbeitung

  1. customThe residue obtained
  2. customis purified by silica gel chromatography with an appropriate solvent mixture
  3. customAfter isolation, removal of the BOC protecting group from the resulting intermediate
  4. concentrationconcentration in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-a6cba76616194c989f8764ce65a83ddd
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08759347B2

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