Phenethylamine → HCID 135494510, compound

HRID 1725561Notes

Reaction equation

HRID 1725561 reaction equation
CO[C:3](=[NH:11])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[OH:10].C(=O)(O)[O-].[Na+].[C:17]1([CH2:23][CH2:24][NH2:25])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[C:26](OC)(=[O:31])[CH2:27][C:28]([CH3:30])=O>CO>[OH:10][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=1[C:3]1[N:25]([CH2:24][CH2:23][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:26](=[O:31])[CH:27]=[C:28]([CH3:30])[N:11]=1

Participants

6

Reactant 4

HCID 1001PhenethylamineHCID 7757Methyl acetoacetateHCID 516892Sodium BicarbonateHCID 13590531026384-76-9

Product 1

HCID 135494510HCID 135494510, compoundYield 22%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-Hydroxy-benzimidic acid methyl ester from step 1a (250 mg, 1.33 mmol) was dissolved in methanol (6 mL) which contained sodium bicarbonate (110 mg, 1.33 mmol). After stirring at room temperature for 30 min, phenylethylamine (165 □I, 1.33 mmol) was added. The mixture was stirred for 4 h at room temperature, and then methyl acetoacetate (1.5 mL) and xylenes (10 mL) were added. Methanol was removed by distillation using a Dean-Stark trap, and the reaction mixture was refluxed for 3 h. The solution was cooled to room temperature and added to dichloromethane (100 mL). The mixture was extracted with water (100 mL) and the organic layer was dried with sodium sulfate containing decolorizing carbon. After filtration and concentration on the rotary evaporator, toluene (10 mL) was added to the residue, and the mixture was placed in the freezer overnight. The precipitate was filtered off and washed with cold toluene (5 mL). The product was further purified by flash chromatography on silica gel (25 g) with ethyl acetate—hexanes (7:3) as an eluent yielding 2-(2-hydroxy-phenyl)-6-methyl-3-phenethyl-3H-pyrimidin-4-one (120 mg, 22%) as a white solid.

Workup

  1. stirringThe mixture was stirred for 4 h at room temperature
  2. customMethanol was removed by distillation
  3. temperaturethe reaction mixture was refluxed for 3 h
  4. temperatureThe solution was cooled to room temperature
  5. additionadded to dichloromethane (100 mL)
  6. extractionThe mixture was extracted with water (100 mL)
  7. dry with materialthe organic layer was dried with sodium sulfate containing decolorizing carbon
  8. filtrationAfter filtration and concentration
  9. customon the rotary evaporator, toluene (10 mL)
  10. additionwas added to the residue
  11. customwas placed in the freezer overnight
  12. filtrationThe precipitate was filtered off
  13. washwashed with cold toluene (5 mL)
  14. customThe product was further purified by flash chromatography on silica gel (25 g) with ethyl acetate—hexanes (7:3) as an eluent

Sources & evidence

ORD record
ord-9bce1227b36044acb1f07995cd3e060f
Source dataset
uspto-grants-2009_02
Patent number
US07491728B2

Reaction notes

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