9-Hydroxy-7-isopropyl-2-(2-propenyl)-3,4-dihydro-2H-pyrazino[1,2-c]pyrimidine-1,6,8(7H)-trione → 9-hydroxy-7-isopropyl-2-(1-propenyl)-3,4-dihydro-2H-pyrazino[1,2-c]pyrimidine-1,6,8(7H)-trione

HRID 1162811Notes

Reaction equation

HRID 1162811 reaction equation
[OH:1][C:2]1[C:7](=[O:8])[N:6]([CH:9]([CH3:11])[CH3:10])[C:5](=[O:12])[N:4]2[CH2:13][CH2:14][N:15]([CH2:18][CH:19]=[CH2:20])[C:16](=[O:17])[C:3]=12>CCO.O.[Rh](Cl)(Cl)Cl>[OH:1][C:2]1[C:7](=[O:8])[N:6]([CH:9]([CH3:10])[CH3:11])[C:5](=[O:12])[N:4]2[CH2:13][CH2:14][N:15]([CH:18]=[CH:19][CH3:20])[C:16](=[O:17])[C:3]=12

Participants

4

Reactant 1

HCID 684317659-Hydroxy-7-isopropyl-2-(2-propenyl)-3,4-dihydro-2H-pyrazino[1,2-c]pyrimidine-1,6,8(7H)-trione

Product 1

HCID 684315469-hydroxy-7-isopropyl-2-(1-propenyl)-3,4-dihydro-2H-pyrazino[1,2-c]pyrimidine-1,6,8(7H)-trione

Reagents, catalysts & solvents 2

HCID 16211510Rhodium trichloride hydrateCatalystHCID 702EthanolSolvent

Procedure

A mixture of 9-hydroxy-7-isopropyl-2-(2-propenyl)-3,4-dihydro-2H-pyrazino[1,2-c]pyrimidine-1,6,8(7H)-trione (3.0 g, 11 mmol) and rhodium trichloride hydrate (200 mg, 1 mmol) in EtOH (75 mL) was heated to reflux for 8 h. The reaction was cooled to ambient temperature and the solvent was removed in vacuo. The reddish solid was triturated in MeOH and collected by filtration to give the title compound as a solid. HPLC RT=2.90 min (Method A); ES MS (M+H)=280; 1H NMR (400 MHz, DMSO-d6) δ 11.59 (s, 1H), 7.10 (d, J=4.5 Hz, 1H), 5.49 (sextet, J=6 Hz, 1H), 5.04 (septet, J=7 Hz, 1H), 3.97 (m, 2H), 3.79 (m, 2H), 1.76 (d, J=6 Hz, 3H), 1.39 (d, J=7 Hz, 6H).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 8 h
  3. customthe solvent was removed in vacuo
  4. customThe reddish solid was triturated in MeOH
  5. filtrationcollected by filtration

Sources & evidence

ORD record
ord-805c836bfd844861a5e86645e41bea7d
Source dataset
uspto-grants-2010_10
Patent number
US07820680B2

Reaction notes

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