HCID 58739055, compound → HCID 58739058, compound

HRID 720296Notes

Reaction equation

HRID 720296 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:7]=[C:8]([N:22]2[CH2:27][CH2:26][N:25]([CH2:28][CH2:29][OH:30])[CH2:24][CH2:23]2)[N:9]([CH3:21])[C:10](=[O:20])[C:11]=1[O:12]CC1C=CC=CC=1)=[O:5])[CH3:2]>CCOC(C)=O.[Pd]>[CH2:1]([O:3][C:4]([C:6]1[N:7]=[C:8]([N:22]2[CH2:23][CH2:24][N:25]([CH2:28][CH2:29][OH:30])[CH2:26][CH2:27]2)[N:9]([CH3:21])[C:10](=[O:20])[C:11]=1[OH:12])=[O:5])[CH3:2]

Participants

4

Reactant 1

HCID 58739055HCID 58739055, compound

Product 1

HCID 58739058HCID 58739058, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 5-benzyloxy-2-[4-(2-hydroxy-ethyl)-piperazin-1-yl]-1-methyl-6-oxo-1,6-dihydro-pyrimidine-4-carboxylic acid ethyl ester (0.2058 g, 0.49 mmol) dissolved in EtOAc (20 mL) was added a small amount of palladium on carbon. The mixture was shaken under H2 at 40 psi for 10 hours, filtered over celite and concentrated to yield the title compound as a yellow waxy solid (0.0483 g, 30% yield). 1H NMR (500 MHz, MeOD) δ: 4.44 (2H, q, J=7.1 Hz), 3.75 (2H, t, J=5.9 Hz), 3.56 (3H, s), 3.22–3.21 (4H, m), 2.78 (4H, bs), 2.68 (2H, t, J=5.9 Hz), 1.41 (3H, t, J=7.2 Hz). HRMS (M+H) calcd for C14H23N4O5: 327.16685. found: 327.1661.

Workup

  1. filtrationfiltered over celite and
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-ac049db4e9c24f5786020f6a408d08ad
Source dataset
uspto-grants-2006_11
Patent number
US07135467B2

Reaction notes

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