Ammonia → HCID 58001709, compound

HRID 420710Notes

Reaction equation

HRID 420710 reaction equation
[C:1]([Cu])#[N:2].Cl[C:5]1[N:10]=[CH:9][C:8]([CH2:11][OH:12])=[CH:7][C:6]=1[CH3:13].CC(OC)(C)C.N>CN(C=O)C>[OH:12][CH2:11][C:8]1[CH:7]=[C:6]([CH3:13])[C:5]([C:1]#[N:2])=[N:10][CH:9]=1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 15413tert-Butyl methyl etherHCID 11686949(6-Chloro-5-methylpyridin-3-yl)methanolHCID 178418546HCID 178418546, compound

Product 1

HCID 58001709HCID 58001709, compoundYield 62.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
250 °C

Procedure

CuCN (54.3 mg, 0.607 mmol) was added to a solution of (6-chloro-5-methyl-3-pyridinyl)methanol (47.8 mg, 0.303 mmol) in anhydrous DMF (2 ml) and the mixture was stirred under microwave irradiation at 250° C. for 35 min. Full conversion was observed by HPLC. TBME and 28% NH3 were added. Extraction, drying (MgSO4), filtration, and removal of the solvent afforded 5-(hydroxymethyl)-3-methyl-2-pyridinecarbonitrile (28.2 mg, 0.190 mmol, 62.8% yield) pure enough to be used in the next step.

Workup

  1. extractionExtraction
  2. customdrying
  3. filtration(MgSO4), filtration, and removal of the solvent

Sources & evidence

ORD record
ord-2318b111d61e457d85375852ba3044b8
Source dataset
uspto-grants-2012_01
Patent number
US08097628B2

Reaction notes

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