Nitrogen → 5-[[[(1,1-Dimethylethyl)dimethylsilyl]oxy]methyl]-2-(methoxymethyl)thiazole

HRID 82829Notes

Reaction equation

N#N.[Si:3]([O:10][CH2:11][C:12]1[S:16][C:15]([CH2:17][OH:18])=[N:14][CH:13]=1)([C:6]([CH3:9])([CH3:8])[CH3:7])([CH3:5])[CH3:4].[CH3:19]I>C(Cl)Cl>[Si:3]([O:10][CH2:11][C:12]1[S:16][C:15]([CH2:17][O:18][CH3:19])=[N:14][CH:13]=1)([C:6]([CH3:9])([CH3:7])[CH3:8])([CH3:5])[CH3:4]

Participants

Conditions

Temperature: 40 °C

Procedure

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of (5-(((tert-butyldimethylsilyl)oxy)methyl)thiazol-2-yl)methanol (1.21 g, 4.65 mmol) in CH2Cl2 (3.0 mL) was treated with MeI (0.35 mL, 5.57 mmol) followed by Ag2O (1.61 g, 6.97 mmol) and the resulting mixture (protected from light) was stirred overnight at 40° C. The reaction mixture was filtered and the solvent was removed under reduced pressure. Purification of the residue by FC (4:1 hept-EA) gave the title compound as a yellow oil: TLC: rf (4:1 hept-EA)=0.27. LC-MS-conditions 07: tR=0.99 min, [M+H]+=273.95.

Workup

filtrationThe reaction mixture was filtered
customthe solvent was removed under reduced pressure
customPurification of the residue by FC (4:1 hept-EA)

Sources & evidence

ORD record: ord-e487a37633ba4dbbbc5fd65b22b1ce20
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08846733B2

Reaction notes

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