N,N-Diethylaniline → 4-Chloro-6-methoxy-2-(4-trifluoromethyl-thiazol-2-yl)-pyrimidine

HRID 880809Notes

Reaction equation

HRID 880809 reaction equation
O[C:2]1[N:7]=[C:6]([C:8]2[S:9][CH:10]=[C:11]([C:13]([F:16])([F:15])[F:14])[N:12]=2)[NH:5][C:4]([O:18][CH3:19])(O)[CH:3]=1.C(N(CC)C1C=CC=CC=1)C.O=P(Cl)(Cl)[Cl:33]>>[Cl:33][C:2]1[CH:3]=[C:4]([O:18][CH3:19])[N:5]=[C:6]([C:8]2[S:9][CH:10]=[C:11]([C:13]([F:16])([F:15])[F:14])[N:12]=2)[N:7]=1

Participants

4

Reactant 3

HCID 7061N,N-DiethylanilineHCID 24813Phosphorus oxychlorideHCID 178494417HCID 178494417, compound

Product 1

HCID 582826704-Chloro-6-methoxy-2-(4-trifluoromethyl-thiazol-2-yl)-pyrimidineYield 45%

Conditions

Temperature
110 °C

Procedure

To a stirred solution of compound 289 (2.38 g, 1 eq.) in POCl3 (7.2 mL) was added N,N-diethylaniline (2.17 g, 1.7 eq.). The mixture was stirred at 110° C. for 16 hrs. The reaction was cooled down to room temperature and poured dropwise into an ice/water mixture. The aqueous solution was extracted with DCM. Organics were dried over Na2SO4, filtered, concentrated under reduced pressure, and purified by silica gel chromatography to yield compound 290 as an orange solid in 45% yield. MS (ESI, EI+): m/z=296 (MH+).

Workup

  1. temperatureThe reaction was cooled down to room temperature
  2. extractionThe aqueous solution was extracted with DCM
  3. dry with materialOrganics were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-e11406a9ac824be4bb0d696878f921b8
Source dataset
uspto-grants-2015_03
Patent number
US08993595B2

Reaction notes

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