Isopropanol → HCID 18173123, compound

HRID 395867Notes

Reaction equation

HRID 395867 reaction equation
[NH2:1][C:2]1[N:7]([CH2:8][CH2:9][CH3:10])[C:6](=[O:11])[N:5]([CH2:12][CH2:13][CH3:14])[C:4](=[O:15])[C:3]=1[NH:16][C:17]([CH:19]1[CH:24]2[CH2:25][CH:21]3[CH:22]([C:23]2=[O:26])[CH:20]13)=O.C(O)(C)C.[OH-].[K+]>O>[O:26]=[C:23]1[CH:22]2[CH:20]3[CH:21]2[CH2:25][CH:24]1[CH:19]3[C:17]1[NH:16][C:3]2[C:4](=[O:15])[N:5]([CH2:12][CH2:13][CH3:14])[C:6](=[O:11])[N:7]([CH2:8][CH2:9][CH3:10])[C:2]=2[N:1]=1

Participants

5

Reactant 3

HCID 3776IsopropanolHCID 14797Potassium HydroxideHCID 86590364HCID 86590364, compound

Product 1

HCID 18173123HCID 18173123, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

5-Oxo-tricyclo[2.2.1.02,6]heptane-3-carboxylic acid (6-amino-2,4-dioxo-1,3-dipropyl-1,2,3,4-tetrahydro-pyrimidin-5-yl)-amide (360 mg) from step 1 was taken in 1:1 isopropanol:water (5 ml) and KOH (84 mg) was added. The reaction mixture was refluxed for one and half-hour. After cooling the reaction mixture to room temperature, iPrOH was removed by rotavap. The aqueous layer was neutralized with 2N HCl and extracted with ethyl acetate (3×50 ml). The combined organic layer was washed with water and brine and dried over Na2SO4. After concentration, the crude product was purified by silica gel chromatography, eluting with ethyl acetate:hexane (1:1). Yield (75 mg) Mass (ES+ 343).

Workup

  1. temperatureThe reaction mixture was refluxed for one and half-hour
  2. customiPrOH was removed by rotavap
  3. extractionextracted with ethyl acetate (3×50 ml)
  4. washThe combined organic layer was washed with water and brine
  5. dry with materialdried over Na2SO4
  6. concentrationAfter concentration
  7. customthe crude product was purified by silica gel chromatography
  8. washeluting with ethyl acetate:hexane (1:1)
  9. customYield (75 mg) Mass (ES+ 343)

Sources & evidence

ORD record
ord-cea97bd33af143809671d736b150539a
Source dataset
uspto-grants-2003_08
Patent number
US06605600B1

Reaction notes

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