(R)-2-Chloro-7-ethyl-8-isopropyl-5-methyl-6-oxo-5,6,7,8-tetrahydropyrimido[4,5-b]pyrazine → (R)-7-ethyl-8-isopropyl-5-methyl-2-(2-oxo-2-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazol-5-yl)ethyl)-7,8-dihydropteridin-6(5H)-one

HRID 44806Notes

Reaction equation

HRID 44806 reaction equation
Cl[C:2]1[N:11]=[CH:10][C:9]2[N:8]([CH3:12])[C:7](=[O:13])[C@@H:6]([CH2:14][CH3:15])[N:5]([CH:16]([CH3:18])[CH3:17])[C:4]=2[N:3]=1.[CH3:19][Si:20]([CH3:34])([CH3:33])[CH2:21][CH2:22][O:23][CH2:24][N:25]1[C:29]([C:30](=[O:32])[CH3:31])=[CH:28][CH:27]=[N:26]1>>[CH2:14]([C@H:6]1[N:5]([CH:16]([CH3:18])[CH3:17])[C:4]2[N:3]=[C:2]([CH2:31][C:30](=[O:32])[C:29]3[N:25]([CH2:24][O:23][CH2:22][CH2:21][Si:20]([CH3:34])([CH3:33])[CH3:19])[N:26]=[CH:27][CH:28]=3)[N:11]=[CH:10][C:9]=2[N:8]([CH3:12])[C:7]1=[O:13])[CH3:15]

Participants

3

Reactant 2

HCID 58405561(R)-2-Chloro-7-ethyl-8-isopropyl-5-methyl-6-oxo-5,6,7,8-tetrahydropyrimido[4,5-b]pyrazineHCID 584059041-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazol-5-yl)ethanone

Product 1

HCID 58405715(R)-7-ethyl-8-isopropyl-5-methyl-2-(2-oxo-2-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazol-5-yl)ethyl)-7,8-dihydropteridin-6(5H)-one

Procedure

Intermediates C-7 was prepared similarly to the synthetic methods used to prepare intermediate B-1, with Intermediate C instead of Intermediate B and with 1-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazol-5-yl)ethanone instead of acetophenone. LCMS: 473.3 m/z (M+H)+.

Workup

  1. customIntermediates C-7 was prepared similarly to the synthetic methods
  2. customto prepare intermediate B-1

Sources & evidence

ORD record
ord-331289c135184cc7b05aedf6ef1d1512
Source dataset
uspto-grants-2013_09
Patent number
US08541418B2

Reaction notes

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