Trimethylsilyldiazomethane → 7-Isopropyl-9-methoxy-3,4-dihydro-2H-pyrazino[1,2-c]pyrimidine-1,6,8(7H)-trione

HRID 1162813Notes

Reaction equation

HRID 1162813 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][NH:15][C:16](=[O:17])[C:3]=12.[CH3:18][Si](C=[N+]=[N-])(C)C>CO.CCOCC>[CH:9]([N:6]1[C:7](=[O:8])[C:2]([O:1][CH3:18])=[C:3]2[C:16](=[O:17])[NH:15][CH2:14][CH2:13][N:4]2[C:5]1=[O:12])([CH3:10])[CH3:11]

Participants

5

Reactant 2

HCID 167693TrimethylsilyldiazomethaneHCID 684329449-Hydroxy-7-isopropyl-3,4-dihydro-2H-pyrazino[1,2-c]pyrimidine-1,6,8(7H)-trione

Product 1

HCID 684325887-Isopropyl-9-methoxy-3,4-dihydro-2H-pyrazino[1,2-c]pyrimidine-1,6,8(7H)-trione

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Procedure

To a solution of 9-hydroxy-7-isopropyl-3,4-dihydro-2H-pyrazino[1,2-c]pyrimidine-1,6,8(7H)-trione (1.0 g, 4.2 mmol) in MeOH (30 mL) was added trimethylsilyldiazomethane (7 mL of a 2.0 M solution in ether, 14 mmol). The mixture was stirred at ambient temperature for 24 h. The solvent was removed in vacuo and the residue was triturated in MeOH and the solid was collected by filtration to give the title compound as a solid. HPLC RT=2.07 min (Method A); ES MS (M+H)=254; 1H NMR (400 MHz, DMSO-d6) δ 8.64 (2, 1H), 5.03 (septet, J=7 Hz, 1H), 3.86 (m, 2H), 3.66 (s, 3H), 3.37 (m, 2H), 1.38 (d, J=7 Hz, 6H).

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue was triturated in MeOH
  3. filtrationthe solid was collected by filtration

Sources & evidence

ORD record
ord-e783733cad5e4304922ea4b4544d7991
Source dataset
uspto-grants-2010_10
Patent number
US07820680B2

Reaction notes

Loading…