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

HRID 1162814Notes

Reaction equation

HRID 1162814 reaction equation
[CH:1]([N:4]1[C:9](=[O:10])[C:8]([O:11][CH3:12])=[C:7]2[C:13](=[O:17])[NH:14][CH2:15][CH2:16][N:6]2[C:5]1=[O:18])([CH3:3])[CH3:2].Cl.Cl[CH2:21][C:22]1[CH:31]=[CH:30][C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[N:23]=1.[H-].[Na+]>CN(C=O)C>[CH:1]([N:4]1[C:9](=[O:10])[C:8]([O:11][CH3:12])=[C:7]2[C:13](=[O:17])[N:14]([CH2:21][C:22]3[CH:31]=[CH:30][C:29]4[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=4)[N:23]=3)[CH2:15][CH2:16][N:6]2[C:5]1=[O:18])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 30838232-(Chloromethyl)quinoline hydrochlorideHCID 684325887-Isopropyl-9-methoxy-3,4-dihydro-2H-pyrazino[1,2-c]pyrimidine-1,6,8(7H)-trione

Product 1

HCID 684305587-Isopropyl-9-methoxy-2-(quinolin-2-ylmethyl)-3,4-dihydro-2H-pyrazino[1,2-c]pyrimidine-1,6,8(7H)-trione

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a cold solution (0° C.) of 7-isopropyl-9-methoxy-3,4-dihydro-2H-pyrazino[1,2-c]pyrimidine-1,6,8(7H)-trione (0.050 g, 0.197 mmol) in DMF (1.5 mL) was added 2-(chloromethyl)quinoline hydrochloride (0.051 g, 0.237 mmol). Sodium hydride (60% suspension in mineral oil, 0.022 g, 0.868 mmol) was added. The mixture was warmed to room temperature and stirred for 24 hours. The reaction mixture was partitioned between water and EtOAc. The organic phase was washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo. The crude product was used in the next step without purification. HPLC RT=3.47 min (Method A); ES MS (M+H)=395.3.

Workup

  1. customThe reaction mixture was partitioned between water and EtOAc
  2. washThe organic phase was washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude product was used in the next step without purification

Sources & evidence

ORD record
ord-863605e91ff14532955a4086c208b5ca
Source dataset
uspto-grants-2010_10
Patent number
US07820680B2

Reaction notes

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