HCID 66590846, compound → HCID 66590676, compound

HRID 1894823Notes

Reaction equation

HRID 1894823 reaction equation
[C:1]([O:5][C:6]([CH2:8][NH:9][C:10]1[CH:11]=[C:12]([C:16]2[CH:17]=[N:18][C:19]([CH:22]=[CH:23][C:24]([O:26][CH3:27])=[O:25])=[N:20][CH:21]=2)[CH:13]=[CH:14][CH:15]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO.[Pd]>[C:1]([O:5][C:6]([CH2:8][NH:9][C:10]1[CH:11]=[C:12]([C:16]2[CH:17]=[N:18][C:19]([CH2:22][CH2:23][C:24]([O:26][CH3:27])=[O:25])=[N:20][CH:21]=2)[CH:13]=[CH:14][CH:15]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 66590846HCID 66590846, compound

Product 1

HCID 66590676HCID 66590676, compoundYield 40%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

30 mg of 10% Pd/C are added to a solution of 0.3 g (0.81 mmol, 1 eq) of methyl 3-{5-[3-(tert-butoxycarbonylmethylamino)phenyl]pyrimidin-2-yl}acrylate (obtained as in 9c) in 3 ml of methanol, in a PARR bomb. The reaction mixture is placed under a hydrogen pressure of 3 bar and is then heated at 50° C. for 12 hours. The reaction medium is cooled to room temperature and then degassed with nitrogen and filtered through Celite. After evaporating off the solvents, the residue is chromatographed on silica gel (90/10 heptane/ethyl acetate). 118.2 mg of methyl 3-{5-[3-(tert-butoxycarbonylmethylamino)phenyl]pyrimidin-2-yl}propanoate are obtained in the form of a colorless oil. Yield=40%.

Workup

  1. temperatureThe reaction medium is cooled to room temperature
  2. customdegassed with nitrogen
  3. filtrationfiltered through Celite
  4. customAfter evaporating off the solvents
  5. customthe residue is chromatographed on silica gel (90/10 heptane/ethyl acetate)

Sources & evidence

ORD record
ord-4f8a9511aae547bf8887c3de54cfd41c
Source dataset
uspto-grants-2013_08
Patent number
US08513297B2

Reaction notes

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