HCID 66869096, compound → HCID 178517475, compound

HRID 474950Notes

Reaction equation

HRID 474950 reaction equation
C[O:2][C:3]1[N:8]=[C:7]([C:9]2[CH:10]=[N:11][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:13][CH:14]=2)[CH:6]=[CH:5][N:4]=1>Cl.O.[OH-].[Na+]>[F:18][C:15]([F:16])([F:17])[C:12]1[N:11]=[CH:10][C:9]([C:7]2[CH:6]=[CH:5][NH:4][C:3](=[O:2])[N:8]=2)=[CH:14][CH:13]=1

Participants

5

Reactant 1

HCID 66869096HCID 66869096, compound

Product 1

HCID 178517475HCID 178517475, compoundYield 75.7%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 962WaterSolventHCID 14798Sodium HydroxideSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 2-methoxy-4-(6-(trifluoromethyl)pyridin-3-yl)pyrimidine (0.35 g, 1.37 mmol) in concentrated HCl (3.0 mL) was heated under reflux for 16 h. The reaction solution was then cooled to 0° C., diluted with water and basified with aqueous sodium hydroxide. The mixture was then extracted with dichloromethane (2×), a 3:1 mixture of chloroform and 2-propanol (3×), ethyl acetate (4×) and ethyl acetate with 5% methanol (3×). The combined organic extract was dried over sodium sulfate and concentrated under reduced pressure to afford the title compound (0.25 g, 75%) as a tan solid: 1H NMR (500 MHz, CD3OD) δ 9.34 (s, 1H), 8.67 (d, J=8.5 Hz, 1H), 8.20 (d, J=6.0 Hz, 1H), 7.93 (d, J=8.5 Hz, 1H), 7.08 (d, J=5.5 Hz, 1H).

Workup

  1. temperatureunder reflux for 16 h
  2. extractionThe mixture was then extracted with dichloromethane (2×)
  3. additiona 3:1 mixture of chloroform and 2-propanol (3×), ethyl acetate (4×) and ethyl acetate with 5% methanol (3×)
  4. extractionThe combined organic extract
  5. dry with materialwas dried over sodium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-90221840b7bc4991834c2227915d8402
Source dataset
uspto-grants-2014_01
Patent number
US08637501B2

Reaction notes

Loading…