Ammonium Hydroxide → 7-methyl-7-phenyl-6,7-dihydro-1H-cyclopenta[d]pyrimidine-2,4(3H,5H)-dione

HRID 475818Notes

Reaction equation

HRID 475818 reaction equation
[CH3:1][C:2]1([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:10]2[O:9][C:8](=O)[NH:7][C:6](=[O:12])[C:5]=2[CH2:4][CH2:3]1.[OH-].[NH4+:20]>>[CH3:1][C:2]1([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:10]2[NH:20][C:8](=[O:9])[NH:7][C:6](=[O:12])[C:5]=2[CH2:4][CH2:3]1

Participants

3

Reactant 2

HCID 14923Ammonium HydroxideHCID 580755937-methyl-7-phenyl-6,7-dihydrocyclopenta[e][1,3]oxazine-2,4(3H,5H)-dione

Product 1

HCID 580756097-methyl-7-phenyl-6,7-dihydro-1H-cyclopenta[d]pyrimidine-2,4(3H,5H)-dioneYield 70%

Conditions

Temperature
80 °C

Procedure

To solid 7-methyl-7-phenyl-6,7-dihydrocyclopenta[e][1,3]oxazine-2,4(3H,5H)-dione (420 mg, 1.727 mmol) was added concentrated Ammonium Hydroxide (4706 μL, 121 mmol) in a sealed tube. The tube was heated for 4 h at 80° C. Cooled to rt. Removed the solvent under a stream of N2. Loaded the residue onto Silica gel and eluted with an EtOAc/Hexane gradient to afford 7-methyl-7-phenyl-6,7-dihydro-1H-cyclopenta[d]pyrimidine-2,4(3H,5H)-dione (293 mg, 1.209 mmol, 70.0% yield). LC-MS (M+H)+=243.1.

Workup

  1. temperatureCooled to rt
  2. customRemoved the solvent under a stream of N2
  3. washeluted with an EtOAc/Hexane gradient

Sources & evidence

ORD record
ord-35d3c8c92a454307a0953beb076c54ed
Source dataset
uspto-grants-2014_01
Patent number
US08637525B2

Reaction notes

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