Cornforth reagent → HCID 86665654, compound

HRID 1399727Notes

Reaction equation

HRID 1399727 reaction equation
[CH3:1][C:2]1[C:7]([CH2:8][OH:9])=[C:6]([C:10]2[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][CH:11]=2)[N:5]=[C:4]([N:17]2[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]2)[N:3]=1.[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=O.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1>ClCCl>[CH3:1][C:2]1[C:7]([CH:8]=[O:9])=[C:6]([C:10]2[CH:11]=[CH:12][C:13]([CH3:16])=[CH:14][CH:15]=2)[N:5]=[C:4]([N:17]2[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]2)[N:3]=1

Participants

4

Reactant 2

HCID 2724130Cornforth reagentHCID 66955971HCID 66955971, compound

Product 1

HCID 86665654HCID 86665654, compoundYield 61.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (4-methyl-2-(piperidin-1-yl)-6-p-tolylpyrimidin-5-yl)methanol (0.800 g; 2,69 mmol) in dichloromethane (27 mL) was added molecular sieves (4 Å) and pyridinium dichromate (1,52 g; 4,04 mmol). The reaction was stirred at room temperature for 21 h. An excess of celite was added to the reaction and the suspension was stirred for 30 min, filtered on a plug of celite and concentrated under reduced pressure. Purification by flash-chromatography on silica gel using a gradient of ethyl acetate (2-20%) in heptane furnished 0.487 g (61%) of the desired compound as a white solid.

Workup

  1. additionAn excess of celite was added to the reaction
  2. stirringthe suspension was stirred for 30 min
  3. filtrationfiltered on a plug of celite
  4. concentrationconcentrated under reduced pressure
  5. customPurification by flash-chromatography on silica gel using a gradient of ethyl acetate (2-20%) in heptane

Sources & evidence

ORD record
ord-f9a311f9e6db406d998003143adc0941
Source dataset
uspto-grants-2014_12
Patent number
US08906906B2

Reaction notes

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