HCID 57976104, compound → HCID 57976099, compound

HRID 1865195Notes

Reaction equation

HRID 1865195 reaction equation
[CH2:1]([O:3][C:4](=[O:33])[CH:5]([C:13]1[C:18]([N+:19]([O-])=O)=[CH:17][N:16]=[C:15]([NH:22][CH:23]2[CH2:28][CH2:27][N:26]([CH2:29][CH2:30][O:31][CH3:32])[CH2:25][CH2:24]2)[N:14]=1)[C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])[CH3:2]>CO.CCOC(C)=O.[Pd]>[CH2:1]([O:3][C:4](=[O:33])[CH:5]([C:13]1[C:18]([NH2:19])=[CH:17][N:16]=[C:15]([NH:22][CH:23]2[CH2:28][CH2:27][N:26]([CH2:29][CH2:30][O:31][CH3:32])[CH2:25][CH2:24]2)[N:14]=1)[C:6]([O:8][C:9]([CH3:11])([CH3:12])[CH3:10])=[O:7])[CH3:2]

Participants

5

Reactant 1

HCID 57976104HCID 57976104, compound

Product 1

HCID 57976099HCID 57976099, compoundYield 99%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-{2-[1-(2-Methoxy-ethyl)-piperidin-4-ylamino]-5-nitro-pyrimidin-4-yl}-malonic acid tert-butyl ester ethyl ester (5, 733 mgs, 1.6 mmol) was dissolved in a mixture of MeOH (15 mls) and EtOAc (5 mls) to which was added 10% Pd/C (137 mgs). The reaction mixture was stirred under an atmosphere of H2 at room temperature and pressure for 2 hrs, filtered through Celite with thorough washing with MeOH and the filtrate concentrated in vacuo to give 2-{5-amino-2-[1-(2-methoxy-ethyl)-piperidin-4-ylamino]-pyrimidin-4-yl}-malonic acid tert-butyl ester ethyl ester (6, 677 mgs, 99%) which was used in the next reaction without further purification. LC/MS Calcd for [M+H]+ 438, found 438.

Workup

  1. filtrationfiltered through Celite
  2. washwith thorough washing with MeOH
  3. concentrationthe filtrate concentrated in vacuo

Sources & evidence

ORD record
ord-eea1d64f40014f9da52635dd91e963ae
Source dataset
uspto-grants-2009_12
Patent number
US07626031B2

Reaction notes

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