Hydrochloric Acid → HCID 135422953, compound

HRID 1725569Notes

Reaction equation

HRID 1725569 reaction equation
[CH3:1][C:2]([NH:16][C:17]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[O:25]C(=O)C)=O)=[C:3]([C:5](=[O:15])[NH:6][CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH3:4].[OH-].[K+].Cl>C(O)C.O>[OH:25][C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=1[C:17]1[N:6]([CH2:7][CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:5](=[O:15])[C:3]([CH3:4])=[C:2]([CH3:1])[N:16]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 68621431HCID 68621431, compound

Product 1

HCID 135422953HCID 135422953, compoundYield 37%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Acetic acid 2-(1-methyl-2-phenethylcarbamoyl-propenylcarbamoyl)-phenyl ester of Example 1f (220 mg, 0.59 mmol) was dissolved in the mixture of ethanol (8 mL) and water (8 mL) which contained 85% potassium hydroxide (0.80 g, 1.2 mmol). The mixture was refluxed overnight. After cooling, the reaction mixture was acidified with hydrochloric acid to pH=1 and extracted with dichloromethane (3×30 mL). The combined organic layers were washed with water (50 mL), brine (50 mL) and dried over anhydrous sodium sulfate. After concentration, the product was purified by flash chromatography on silica gel (39 g) eluting with hexanes-ethyl acetate (1:1) to give 2-(2-hydroxy-phenyl)-5,6-dimethyl-3-phenethyl-3H-pyrimidin-4-one (70 mg, 37%) as a white solid.

Workup

  1. temperatureThe mixture was refluxed overnight
  2. temperatureAfter cooling
  3. extractionextracted with dichloromethane (3×30 mL)
  4. washThe combined organic layers were washed with water (50 mL), brine (50 mL)
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationAfter concentration
  7. customthe product was purified by flash chromatography on silica gel (39 g)
  8. washeluting with hexanes-ethyl acetate (1:1)

Sources & evidence

ORD record
ord-69c21a1edf5a4689b690c30336c6a475
Source dataset
uspto-grants-2009_02
Patent number
US07491728B2

Reaction notes

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