Hydrochloric Acid → 2-[4-(Trifluoromethoxy)phenyl]-5-pyrimidinol

HRID 2066635Notes

Reaction equation

HRID 2066635 reaction equation
C(OC[O:5][C:6]1[CH:7]=[N:8][C:9]([C:12]2[CH:17]=[CH:16][C:15]([O:18][C:19]([F:22])([F:21])[F:20])=[CH:14][CH:13]=2)=[N:10][CH:11]=1)C.Cl>CO.O>[F:22][C:19]([F:20])([F:21])[O:18][C:15]1[CH:16]=[CH:17][C:12]([C:9]2[N:8]=[CH:7][C:6]([OH:5])=[CH:11][N:10]=2)=[CH:13][CH:14]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 669560465-(Ethoxymethoxy)-2-[4-(trifluoromethoxy)phenyl]pyrimidine

Product 1

HCID 669564972-[4-(Trifluoromethoxy)phenyl]-5-pyrimidinolYield 99%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Ether 110 (379 mg, 1.21 mmol) was treated with 1.25M HCl in MeOH (11 mL) and the mixture was stirred at room temperature for 12 h, and then at 53° C. for 2 h. The resulting cooled solution was diluted with water (50 mL) and extracted with CH2Cl2 (5×50 mL). The combined extracts were evaporated to dryness and the residue was triturated in pentane to give 2-[4-(trifluoromethoxy)phenyl]-5-pyrimidinol (112) (305 mg, 99%) as a white solid: mp (pentane) 156-157° C.; 1H NMR (CDCl3) δ 8.45 (s, 2H), 8.38 (dt, J=8.9, 2.4 Hz, 2H), 7.29 (br dd, J=8.9, 0.7 Hz, 2H), 5.60 (br s, 1H); HRESIMS calcd for C11H8F3N2O2 m/z [M+H]+ 257.0532. found 257.0526.

Workup

  1. waitat 53° C. for 2 h
  2. temperatureThe resulting cooled solution
  3. extractionextracted with CH2Cl2 (5×50 mL)
  4. customThe combined extracts were evaporated to dryness
  5. customthe residue was triturated in pentane

Sources & evidence

ORD record
ord-16652400950a49a7a86bd4ddbb45b5f3
Source dataset
uspto-grants-2012_10
Patent number
US08293734B2

Reaction notes

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