Hydrochloric Acid → HCID 15095345, compound

HRID 2066633Notes

Reaction equation

HRID 2066633 reaction equation
C(OC[O:5][C:6]1[CH:7]=[N:8][C:9]([C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)=[N:10][CH:11]=1)C.Cl>CO>[F:18][C:15]1[CH:14]=[CH:13][C:12]([C:9]2[N:8]=[CH:7][C:6]([OH:5])=[CH:11][N:10]=2)=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 669571525-(Ethoxymethoxy)-2-(4-fluorophenyl)pyrimidine

Product 1

HCID 15095345HCID 15095345, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
53 °C

Procedure

Ether 109 (301 mg, 1.21 mmol) was treated with 1.25M HCl in MeOH (10 mL) and the mixture was stirred at 53° C. for 4 h. The resulting cooled solution was diluted with ice-water (100 mL) and extracted with CH2Cl2 (5×80 mL). The combined extracts were evaporated to dryness and the residue was triturated in pentane to give 2-(4-fluorophenyl)-5-pyrimidinol (111) (225 mg, 98%) as a white solid: mp (pentane) 200-202° C.; 1H NMR [(CD3)2SO] δ 10.55 (v br s, 1H), 8.42 (s, 2H), 8.29 (ddt, J=9.1, 5.7, 2.6 Hz, 2H), 7.28 (ft, J=9.0, 2.6 Hz, 2H); HRESIMS calcd for C10H8FN2O m/z [M+H]+ 191.0615. found 191.0616.

Workup

  1. temperatureThe resulting cooled solution
  2. extractionextracted with CH2Cl2 (5×80 mL)
  3. customThe combined extracts were evaporated to dryness
  4. customthe residue was triturated in pentane

Sources & evidence

ORD record
ord-70fb113c731f45a8adf351e5f2781001
Source dataset
uspto-grants-2012_10
Patent number
US08293734B2

Reaction notes

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