Trimethylsilyldiazomethane → [5-(4-Chloro-benzyloxy)-4-methoxy-pyridin-2-yl]-methanol

HRID 1098468Notes

Reaction equation

HRID 1098468 reaction equation
[Cl:1][C:2]1[CH:18]=[CH:17][C:5]([CH2:6][O:7][C:8]2[C:9](=[O:16])[CH:10]=[C:11]([CH2:14][OH:15])[NH:12][CH:13]=2)=[CH:4][CH:3]=1.[CH3:19][Si](C=[N+]=[N-])(C)C>CO.CN(C)C=O.CCCCCC>[Cl:1][C:2]1[CH:18]=[CH:17][C:5]([CH2:6][O:7][C:8]2[C:9]([O:16][CH3:19])=[CH:10][C:11]([CH2:14][OH:15])=[N:12][CH:13]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 2

HCID 167693Trimethylsilyldiazomethane2×HCID 580875645-(4-chloro-benzyloxy)-2-hydroxymethyl-1H-pyridin-4-one

Product 1

HCID 58087092[5-(4-Chloro-benzyloxy)-4-methoxy-pyridin-2-yl]-methanol

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6228DimethylformamideSolventHCID 8058HexaneSolvent2×

Procedure

5-(4-Chloro-benzyloxy)-2-hydroxymethyl-1H-pyridin-4-one (639, 1.06 g, 3.99 mmol) was dissolved in methanol (8.5 mL) and N,N-dimethylformamide (46 mL). Trimethylsilyldiazomethane in hexane (2.00 M, 3.99 mL) was added. The reaction was stirred at room temperature overnight, then additional trimethylsilyldiazomethane in hexane (2.00 M, 3.99 mL) was added. The reaction was stirred at room temperature for 2 days. The mixture was adsorbed onto silica and purified by silica gel chromatography, methanol:dichloromethane to provide the compound (640, 798 mg, 72%). MS (ESI) [M−H+]+=280.4, 282.4.

Workup

  1. stirringThe reaction was stirred at room temperature for 2 days
  2. custompurified by silica gel chromatography, methanol
  3. customdichloromethane to provide the compound (640, 798 mg, 72%)

Sources & evidence

ORD record
ord-538ab5c520864614b1593d931b950c91
Source dataset
uspto-grants-2012_03
Patent number
US08143271B2

Reaction notes

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