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 1008937Notes

Reaction equation

HRID 1008937 reaction equation
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

Participants

3

Reactant 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

Product 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

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-c09ed877061f4da28cc269468af6e630
Source dataset
uspto-grants-2011_07
Patent number
US07973035B2

Reaction notes

Loading…