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 340585Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 340585
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-135cba156e134e138f0264b63856b3d9
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08895584B2

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