2,6-Lutidine → HCID 58941848, compound

HRID 1845766Notes

Reaction equation

[OH:1][CH2:2][C:3]1[S:7][N:6]=[N:5][C:4]=1[C:8]([O:10][CH3:11])=[O:9].N1C(C)=CC=CC=1C.O([Si:28]([CH:35]([CH3:37])[CH3:36])([CH:32]([CH3:34])[CH3:33])[CH:29]([CH3:31])[CH3:30])S(C(F)(F)F)(=O)=O>C(Cl)Cl>[CH:29]([Si:28]([CH:35]([CH3:37])[CH3:36])([CH:32]([CH3:34])[CH3:33])[O:1][CH2:2][C:3]1[S:7][N:6]=[N:5][C:4]=1[C:8]([O:10][CH3:11])=[O:9])([CH3:31])[CH3:30]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of methyl 5-(hydroxymethyl)-1,2,3-thiadiazole-4-carboxylate (1.22 g, 0.007 mol) in DCM (20 mL) at 0° C. was added 2,6-lutidine (2.0 mL, 0.018 mol) followed by triisopropylsilyl triflate (2.4 mL, 0.0091 mol). The solution was stirred at 0° C. for 5 minutes. The reaction was then concentrated and purified by flash chromatography to give the desired product (2.0 g, 87%). 1H NMR (400 MHz, CDCl3): δ□; MF=C14H26N2O3SSi; LCMS calculated for C14H27N2O3SSi (M+H)+: m/z 331.1.

Workup

concentrationThe reaction was then concentrated
custompurified by flash chromatography

Sources & evidence

ORD record: ord-3a645367f9f54abdad85b032708e9fa2
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08951536B2

Reaction notes

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