Hydrochloric Acid → HCID 136148285, compound

HRID 1373777Notes

Reaction equation

HRID 1373777 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:18])[CH2:9][C:10]2[CH:15]=[CH:14][N:13]=[C:12]([S:16][CH3:17])[N:11]=2)=[CH:4][CH:3]=1.[N:19](OC(C)(C)C)=[O:20].Cl>C(O)C.C(O)CC>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:18])/[C:9](=[N:19]\[OH:20])/[C:10]2[CH:15]=[CH:14][N:13]=[C:12]([S:16][CH3:17])[N:11]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 10906Tert-Butyl nitriteHCID 117474161-(4-Fluorophenyl)-2-[2-(methylsulfanyl)pyrimidin-4-yl]ethan-1-one2×

Product 1

HCID 136148285HCID 136148285, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 10311-PropanolSolvent

Procedure

To a suspension of 1-(4-fluorophenyl)-2-(2-(methylthio)pyrimidin-4-yl)ethanone, 73 (1.0 g) in ethanol (20 mL) at −10° C., under an atmosphere of nitrogen, is added dropwise t-butyl nitrite (0.5 mL) followed by hydrogen chloride in n-propanol (2.5 to 3 N, 0.6 mL) while maintaining the temperature below −5° C. Once the addition is complete, the solution is allowed to warm to room temperature with stirring and after 2 h the solvent is evaporated and the residue partitioned between saturated aqueous sodium hydrogen carbonate and ethyl acetate. The layers are separated; the aqueous phase is extracted with ethyl acetate and the combined organic phases dried over sodium sulfate. Filtration and evaporation of the solvent affords the title compound, 74 (1.0 g).

Workup

  1. temperaturewhile maintaining the temperature below −5° C
  2. additionOnce the addition
  3. customis evaporated
  4. customthe residue partitioned between saturated aqueous sodium hydrogen carbonate and ethyl acetate
  5. customThe layers are separated
  6. extractionthe aqueous phase is extracted with ethyl acetate
  7. dry with materialthe combined organic phases dried over sodium sulfate
  8. filtrationFiltration and evaporation of the solvent

Sources & evidence

ORD record
ord-fbc59ea81780425cafb1d95e46094d80
Source dataset
uspto-grants-2007_01
Patent number
US07163945B2

Reaction notes

Loading…