4-((1S)-2-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}-1-{[(phenylmethyl)oxy]methyl}ethyl)-6-(methyloxy)-1,4-dihydropyrido[2,3-b]pyrazin-3(2H)-one → 4-[(1S)-2-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}-1-(hydroxymethyl)ethyl]-6-(methyloxy)-1,4-dihydropyrido[2,3-b]pyrazin-3(2H)-one

HRID 420689Notes

Reaction equation

[CH3:1][C:2]([Si:5]([CH3:32])([CH3:31])[O:6][CH2:7][C@@H:8]([N:18]1[C:23](=[O:24])[CH2:22][NH:21][C:20]2[CH:25]=[CH:26][C:27]([O:29][CH3:30])=[N:28][C:19]1=2)[CH2:9][O:10]CC1C=CC=CC=1)([CH3:4])[CH3:3]>[OH-].[OH-].[Pd+2].CCO.[Pd]>[CH3:4][C:2]([Si:5]([CH3:31])([CH3:32])[O:6][CH2:7][C@@H:8]([N:18]1[C:23](=[O:24])[CH2:22][NH:21][C:20]2[CH:25]=[CH:26][C:27]([O:29][CH3:30])=[N:28][C:19]1=2)[CH2:9][OH:10])([CH3:1])[CH3:3]

Participants

Conditions

Temperature: 50 °C

Procedure

A mixture of 4-((1S)-2-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}-1-{[(phenylmethyl)oxy]methyl}ethyl)-6-(methyloxy)-1,4-dihydropyrido[2,3-b]pyrazin-3(2H)-one (250.4 g, 0.547 mol), Pearlman's catalyst (25 g) and 10% Pd/C (25 g, 50% wet) in EtOH (5 L) was stirred at 50° C. under 5 bar of H2 for 3.5 h. The reaction mixture was filtered through celite and the filtrate was evaporated to give 4-[(1S)-2-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}-1-(hydroxymethyl)ethyl]-6-(methyloxy)-1,4-dihydropyrido[2,3-b]pyrazin-3(2H)-one (191.2 g, 95%) as a dark blue solid.

Workup

filtrationThe reaction mixture was filtered through celite
customthe filtrate was evaporated

Sources & evidence

ORD record: ord-cec66e55420347b6acbc32f23f47de7b
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08097628B2

Reaction notes

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