Acetonitrile → HCID 53379812, compound

HRID 625943Notes

Reaction equation

HRID 625943 reaction equation
[CH2:1]([N:8]1[CH:12]=[C:11]([C:13]2[CH:14]=[C:15]([O:21]COCC[Si](C)(C)C)[C:16](=[O:20])[N:17]([CH3:19])[CH:18]=2)[N:10]=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.F[B-](F)(F)F.[Li+].C(#N)C>>[CH2:1]([N:8]1[CH:12]=[C:11]([C:13]2[CH:14]=[C:15]([OH:21])[C:16](=[O:20])[N:17]([CH3:19])[CH:18]=2)[N:10]=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 6342AcetonitrileHCID 4298216Lithium tetrafluoroborateHCID 866754875-(1-benzyl-1H-1,2,3-triazol-4-yl)-1-methyl-3-{[2-(trimethylsilyl)ethoxy]methoxy}pyridin-2(1H)-one

Product 1

HCID 53379812HCID 53379812, compoundYield 43%

Procedure

To a solution of containing 5-(1-benzyl-1H-1,2,3-triazol-4-yl)-1-methyl-3-{[2-(trimethylsilyl)ethoxy]methoxy}pyridin-2(1H)-one (148 mg, 0.359 mmol) in 1 mL THE was added 1.1 mL of a 1 M solution of lithium tetrafluoroborate in acetonitrile (1.1 mmol). This mixture was microwaved in a sealed vial at 100° C. for 10 minutes. After cooling, the mixture was evaporated under reduced pressure and purified by reversed-phase HPLC to afford 5-(1-benzyl-1H-1,2,3-triazol-4-yl)-3-hydroxy-1-methylpyridin-2(1H)-one (43.5 mg, 0.154 mmol, 43% yield). 1H NMR δ (ppm) (DMSO-d6): 9.28 (1 H, s), 8.38 (1 H, s), 7.75 (1 H, d, J=2.20 Hz), 7.42-7.31 (5 H, m), 5.61 (2 H, s), 3.53 (3 H, s). High resolution mass spec (ESI) calc (M+H)+=283.1190 found 283.1188.

Workup

  1. customThis mixture was microwaved in a sealed vial at 100° C. for 10 minutes
  2. temperatureAfter cooling
  3. customthe mixture was evaporated under reduced pressure
  4. custompurified by reversed-phase HPLC

Sources & evidence

ORD record
ord-faec96bfc48e489dab73910c511bd926
Source dataset
uspto-grants-2016_04
Patent number
US09309199B2

Reaction notes

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