(S)-tert-butyl 1-(6-(4-(benzyloxy)pyrimidin-2-yl)quinolin-4-yl)piperidin-3-ylcarbamate → (S)-tert-butyl 1-(6-(6-oxo-1,6-dihydropyrimidin-2-yl)quinolin-4-yl)piperidin-3-ylcarbamate

HRID 1028061Notes

Reaction equation

HRID 1028061 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][N:12]=[C:11]([C:15]2[CH:16]=[C:17]3[C:22](=[CH:23][CH:24]=2)[N:21]=[CH:20][CH:19]=[C:18]3[N:25]2[CH2:30][CH2:29][CH2:28][C@H:27]([NH:31][C:32](=[O:38])[O:33][C:34]([CH3:37])([CH3:36])[CH3:35])[CH2:26]2)[N:10]=1)C1C=CC=CC=1>[Pd].CCO.CCOC(C)=O>[O:8]=[C:9]1[NH:10][C:11]([C:15]2[CH:16]=[C:17]3[C:22](=[CH:23][CH:24]=2)[N:21]=[CH:20][CH:19]=[C:18]3[N:25]2[CH2:30][CH2:29][CH2:28][C@H:27]([NH:31][C:32](=[O:38])[O:33][C:34]([CH3:36])([CH3:35])[CH3:37])[CH2:26]2)=[N:12][CH:13]=[CH:14]1

Participants

4

Reactant 1

HCID 67338681(S)-tert-butyl 1-(6-(4-(benzyloxy)pyrimidin-2-yl)quinolin-4-yl)piperidin-3-ylcarbamate

Product 1

HCID 67309483(S)-tert-butyl 1-(6-(6-oxo-1,6-dihydropyrimidin-2-yl)quinolin-4-yl)piperidin-3-ylcarbamateYield 87%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21584252Ethanol ethylacetateSolvent

Procedure

To a solution of (S)-tert-butyl 1-(6-(4-(benzyloxy)pyrimidin-2-yl)quinolin-4-yl)piperidin-3-ylcarbamate (1.0 equiv.) in 4:1 EtOH/EtOAc (0.6 M), was added 10% palladium on carbon (0.2 eq.). The resulting heterogeneous solution was stirred for 12 hours under an atmosphere of hydrogen. The mixture was then filtered through a pad of celite eluting with EtOAc. The volatiles were removed in vacuo yielding (S)-tert-butyl 1-(6-(6-oxo-1,6-dihydropyrimidin-2-yl)quinolin-4-yl)piperidin-3-ylcarbamate (87%). LCMS (m/z): 422.1 (MH+); LC Rt=2.14 min.

Workup

  1. filtrationThe mixture was then filtered through a pad of celite
  2. washeluting with EtOAc
  3. customThe volatiles were removed in vacuo

Sources & evidence

ORD record
ord-d05cf2df125d4d5d8b1a5487acdb0391
Source dataset
uspto-grants-2014_05
Patent number
US08735424B2

Reaction notes

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