Hydrochloric Acid → HCID 23295707, compound

HRID 1953968Notes

Reaction equation

HRID 1953968 reaction equation
[F:1][C:2]([F:36])([F:35])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:14]=[C:13]([O:15][C:16]3[CH:20]=[C:19]([C:21]([F:24])([F:23])[F:22])[S:18][CH:17]=3)[CH:12]=[C:11]([O:25][C:26]3C=C(C(F)(F)F)SC=3)[N:10]=2)=[CH:5][CH:4]=1.O(C)[Na].CO.Cl>CN(C)C=O>[CH3:26][O:25][C:11]1[CH:12]=[C:13]([O:15][C:16]2[CH:20]=[C:19]([C:21]([F:23])([F:24])[F:22])[S:18][CH:17]=2)[N:14]=[C:9]([C:6]2[CH:5]=[CH:4][C:3]([C:2]([F:35])([F:1])[F:36])=[CH:8][CH:7]=2)[N:10]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 23295687HCID 23295687, compoundHCID 178418582HCID 178418582, compound

Product 1

HCID 23295707HCID 23295707, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A solution of 2-(α,α,α-trifluoro-p-tolyl)-4,6-di{[5-(trifluoromethyl)-3-thienyl]oxy}pyrimidine (1.50 g, 2.70 mnol) in dimethylformamide is treated with 25% NaOCH3 in methanol (0.58 g, 2.70 mmol), heated to 60° C. for 1.5 hours, cooled to room temperature, poured onto water and acidified to pH 5 with 6N HCl. The resultant reaction mixture is extracted with ether. The ether extracts are combined, washed sequentially with water and brine, dried over MgSO4 and concentrated in vacuo to give a solid residue. The residue is chromatographed (silica gel, ethyl acetate/hexanes, 3/97) to afford the title product as a white solid, 0.58 g (51% yield), mp 91-93° C., identified by 1HNMR, 13CNMR, 19FNMR, mass spectral and elemental analyses.

Workup

  1. temperaturecooled to room temperature
  2. additionpoured onto water
  3. customThe resultant reaction mixture
  4. extractionis extracted with ether
  5. washwashed sequentially with water and brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated in vacuo
  8. customto give a solid residue
  9. customThe residue is chromatographed (silica gel, ethyl acetate/hexanes, 3/97)

Sources & evidence

ORD record
ord-f746f030cd064a33bc59ead078174659
Source dataset
uspto-grants-2000_09
Patent number
US06121202

Reaction notes

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