Chloromethyl Methyl Ether → 4-[3-{[tert-Butyl(dimethyl)silyl]oxy}-2-(methoxymethoxy)propyl]-6-methoxypyrido[2,3-b]pyrazin-3(4H)-one

HRID 1847051Notes

Reaction equation

HRID 1847051 reaction equation
C(N(CC)C(C)C)(C)C.Cl[CH2:11][O:12][CH3:13].[Si:14]([O:21][CH2:22][CH:23]([OH:38])[CH2:24][N:25]1[C:30](=[O:31])[CH:29]=[N:28][C:27]2[CH:32]=[CH:33][C:34]([O:36][CH3:37])=[N:35][C:26]1=2)([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15]>ClCCl>[Si:14]([O:21][CH2:22][CH:23]([O:38][CH2:11][O:12][CH3:13])[CH2:24][N:25]1[C:30](=[O:31])[CH:29]=[N:28][C:27]2[CH:32]=[CH:33][C:34]([O:36][CH3:37])=[N:35][C:26]1=2)([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:15])[CH3:16]

Participants

5

Reactant 3

HCID 7864Chloromethyl Methyl EtherHCID 81531DiisopropylethylamineHCID 867249764-(3-{[tert-Butyl(dimethyl)silyl]oxy}-2-hydroxypropyl)-6-methoxypyrido[2,3-b]pyrazin-3(4H)-one

Product 1

HCID 867249774-[3-{[tert-Butyl(dimethyl)silyl]oxy}-2-(methoxymethoxy)propyl]-6-methoxypyrido[2,3-b]pyrazin-3(4H)-oneYield 67.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

N,N-Diisopropylethylamine (1.93 ml, 11.10 mmol) and chloromethylmethyl ether (0.56 ml, 7.40 mmol) were added under cooling on ice to a solution of 4-(3-{[tert-butyl(dimethyl)silyl]oxy}-2-hydroxypropyl)-6-methoxypyrido[2,3-b]pyrazin-3(4H)-one (1.35 g, 3.70 mmol) in dichloromethane (20 ml) and the mixture was stirred for 24 hours. The reaction solution was diluted with dichloromethane and washed with water. The organic layer was dried over anhydrous sodium sulfate, the solvent was removed under reduced pressure and the residue was purified by silica gel column chromatography (hexane/ethyl acetate) to yield 1.02 g (67%) of the title compound in the form of a yellow oily product.

Workup

  1. washwashed with water
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. customthe solvent was removed under reduced pressure
  4. customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-79cc8392f1d741b2a80ea68bb89dc631
Source dataset
uspto-grants-2015_02
Patent number
US08952010B2

Reaction notes

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