Methanol → HCID 86343533, compound

HRID 2202413Notes

Reaction equation

HRID 2202413 reaction equation
[NH2:1][C:2]1[C:7]([CH3:8])=[CH:6][N:5]=[C:4]([Cl:9])[CH:3]=1.[OH:10][C:11]1[CH:16]=[C:15]([CH3:17])[O:14][C:13](=O)[CH:12]=1.[Cl-].[Li+].CO>ClCCl>[Cl:9][C:4]1[CH:3]=[C:2]([N:1]2[C:15]([CH3:17])=[CH:16][C:11]([OH:10])=[CH:12][C:13]2=[O:14])[C:7]([CH3:8])=[CH:6][N:5]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 433294Lithium ChlorideHCID 126437062-Chloro-5-methylpyridin-4-amineHCID 546757574-Hydroxy-6-methyl-2-pyrone

Product 1

HCID 86343533HCID 86343533, compoundYield 6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
160 °C

Procedure

A well-powdered mixture of 4-amino-5-methyl-2-chloropyridine (0.5 g, 3.5 mmol), 4-hydroxy-6-methyl-pyrone (0.665 g, 5.3 mmol), and lithium chloride (0.025 g, 0.6 mmol) was heated at 160° C. for 20 min in a sealed tube. The resulting melt was cooled and the product was isolated by silica gel flash chromatography using 3% methanol in dichloromethane. Appropriate fractions were combined, concentrated under reduced pressure and the resulting solid was triturated with ethyl acetate, cooled and filtered. The solid was washed with ethyl acetate and dried to give 0.053 g of the title compound as a yellow powder. ES-MS: m/z=251 (M+H).

Workup

  1. temperatureThe resulting melt was cooled
  2. customthe product was isolated by silica gel flash chromatography
  3. concentrationconcentrated under reduced pressure
  4. customthe resulting solid was triturated with ethyl acetate
  5. temperaturecooled
  6. filtrationfiltered
  7. washThe solid was washed with ethyl acetate
  8. customdried

Sources & evidence

ORD record
ord-e40d97fec96f4f4192d6ee5392833acd
Source dataset
uspto-grants-2016_06
Patent number
US09365546B2

Reaction notes

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