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

HRID 250651Notes

Reaction equation

HRID 250651 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-2299ee4ed7a54e62953d71ce7c709e1a
Source dataset
uspto-grants-2011_01
Patent number
US07863288B2

Reaction notes

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