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

HRID 1162812Notes

Reaction equation

HRID 1162812 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](C=CC)[C:16](=[O:17])[C:3]=12>CO.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][NH:15][C:16](=[O:17])[C:3]=12

Participants

4

Reactant 1

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Procedure

A solution of 9-hydroxy-7-isopropyl-2-(1-propenyl)-3,4-dihydro-2H-pyrazino[1,2-c]pyrimidine-1,6,8(7H)-trione (1.8 g, 6.4 mmol) in MeOH (15 mL) and 6 N aqueous HCl (10 mL) was heated to reflux for 1 h. The solvents were removed in vacuo and the residue was triturated in MeOH to give the title compound as a solid. HPLC RT=2.14 min (Method A); ES MS (M+H)=240; 1H NMR (400 MHz, DMSO-d6) δ 11.5 (v broad s, 1H), 9.19 (s, 1H), 5.04 (septet, J=7 Hz, 1H), 3.87 (t, J=7 Hz, 2H), 3.46 (m, 2H), 1.38 (d, J=7 Hz, 6H).

Workup

  1. temperatureto reflux for 1 h
  2. customThe solvents were removed in vacuo
  3. customthe residue was triturated in MeOH

Sources & evidence

ORD record
ord-8bd03b126b8c466b9f141a1427ef344f
Source dataset
uspto-grants-2010_10
Patent number
US07820680B2

Reaction notes

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