Hydrochloric Acid → HCID 11245973, compound

HRID 1725571Notes

Reaction equation

HRID 1725571 reaction equation
C1([Mg]Br)C=CC=CC=1.[F:9][C:10]1[CH:11]=[C:12]([CH:16]=[CH:17][CH:18]=1)[CH2:13][CH2:14][NH2:15].C[O:20][C:21](=O)[CH:22]([CH:36]([CH3:38])[CH3:37])[C:23]([NH:25][C:26](=O)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[O:33][CH3:34])=[CH2:24].Cl>C1(C)C=CC=CC=1.C(OCC)(=O)C>[F:9][C:10]1[CH:11]=[C:12]([CH2:13][CH2:14][N:15]2[C:21](=[O:20])[C:22]([CH:36]([CH3:37])[CH3:38])=[C:23]([CH3:24])[N:25]=[C:26]2[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[O:33][CH3:34])[CH:16]=[CH:17][CH:18]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 5339282-(3-Fluorophenyl)ethanamineHCID 58921890HCID 58921890, compoundHCID 178418255HCID 178418255, compound

Product 1

HCID 11245973HCID 11245973, compoundYield 46%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
20 °C

Procedure

Phenyl magnesium bromide (1M solution in THF, 0.0021 mol) was added to a solution of 3-fluoro-phenethyl amine (0.27 mL, 0.0021 mol) in anhydrous toluene (20 mL). After stirring the mixture at 20° C. for 10 min, 2-isopropyl-3-(2-methoxy-benzoylamino)-but-3-enoic acid methyl ester of step (b) above in this method (Method B of Example 13) (0.05 g, 0.0017 mol) was added. The mixture was refluxed for 10 hours, cooled and ethyl acetate (50 mL) was added followed by 1N HCl (50 mL). The organic layer was separated and the aqueous layer was extracted with EtOAc (3×50 mL). The combined organic extracts were washed with 1N HCl (3×100 mL), water (100 mL), and brine (100 mL). After drying over sodium sulfate and concentration on a rotatory evaporator, the product was purified by column chromatography over silica gel (200-400 mesh) eluting with 12% EtOAc/hexanes to give 3-[2-(3-fluoro-phenyl)-ethyl]-5-isopropyl-2-(2-methoxy-phenyl)-6-methyl-3H-pyrimidin-4-one (0.3 g, 46%) as a white solid.

Workup

  1. temperatureThe mixture was refluxed for 10 hours
  2. temperaturecooled
  3. customThe organic layer was separated
  4. extractionthe aqueous layer was extracted with EtOAc (3×50 mL)
  5. washThe combined organic extracts were washed with 1N HCl (3×100 mL), water (100 mL), and brine (100 mL)
  6. dry with materialAfter drying over sodium sulfate and concentration on a rotatory evaporator
  7. customthe product was purified by column chromatography over silica gel (200-400 mesh)
  8. washeluting with 12% EtOAc/hexanes

Sources & evidence

ORD record
ord-982f8ae4993f41619c36dcc3beea3d16
Source dataset
uspto-grants-2009_02
Patent number
US07491728B2

Reaction notes

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