4-Methoxyphenol → HCID 58247423, compound

HRID 860764Notes

Reaction equation

HRID 860764 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[C:5]([Cl:9])=[CH:4][N:3]=1.[CH3:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=1.C(=O)([O-])[O-].[K+].[K+]>CN1C(=O)CCC1>[Cl:1][C:2]1[N:7]=[C:6]([O:18][C:15]2[CH:16]=[CH:17][C:12]([O:11][CH3:10])=[CH:13][CH:14]=2)[C:5]([Cl:9])=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 90154-MethoxyphenolHCID 11430Potassium CarbonateHCID 2372592,4,5-Trichloropyrimidine

Product 1

HCID 58247423HCID 58247423, compoundYield 94.3%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A solution of 2,4,5-trichloropyrimidine (1.0 g, 5.4 mmol) and 4-methoxyphenol (0.64 g, 5.2 mmol) in NMP (2.5 ml) was treated with anhydrous potassium carbonate (1.65 g, 12 mmol). The reaction mixture was allowed to stir at ambient temperature for 18 hours. The reaction was partitioned between water and ethyl acetate. The organic layer was evaporated and the residue purified by column chromatography eluting with 10% ethyl acetate in isohexane to afford a solid product (1.33 g, 90%). NMR: 3.78 (s, 3H), 7.00 (d, 2H), 7.20 (d, 2H), 8.77 (s, 1H); MS (M+H)+271, 273.

Workup

  1. customThe reaction was partitioned between water and ethyl acetate
  2. customThe organic layer was evaporated
  3. customthe residue purified by column chromatography
  4. washeluting with 10% ethyl acetate in isohexane

Sources & evidence

ORD record
ord-20ee45d51318413db9f71cf41ec4d5d5
Source dataset
uspto-grants-2006_12
Patent number
US07153964B2

Reaction notes

Loading…