Sodium Hydroxide → 4-benzyloxycarbonyl-3-(S)-methoxymethyl-1-[(2-methylthiopyrimidin-5-yl)-methyl]-piperazine-2-one

HRID 1433101Notes

Reaction equation

HRID 1433101 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][NH:14][C:13](=[O:17])[C@@H:12]1[CH2:18][O:19][CH3:20])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[CH2:22][C:23]1[CH:24]=[N:25][C:26]([S:29][CH3:30])=[N:27][CH:28]=1.[OH-].[Na+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.ClCCl.O>[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][N:14]([CH2:22][C:23]2[CH:24]=[N:25][C:26]([S:29][CH3:30])=[N:27][CH:28]=2)[C:13](=[O:17])[C@@H:12]1[CH2:18][O:19][CH3:20])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 14798Sodium HydroxideHCID 60209911HCID 60209911, compoundHCID 688982614-Benzyloxycarbonyl-3-(S)-methoxymethyl-piperazine-2-one

Product 1

HCID 689003764-benzyloxycarbonyl-3-(S)-methoxymethyl-1-[(2-methylthiopyrimidin-5-yl)-methyl]-piperazine-2-oneYield 33%

Reagents, catalysts & solvents 3

HCID 74236Tetrabutylammonium BromideCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

4-Benzyloxycarbonyl-3-(S)-methoxymethyl-piperazine-2-one (0.1 g 0.37 mmol), 5-bromomethyl-2-methylthiopyrimidine (0.08 g, 0.37 mmol) and tetra-n-butylammonium bromide (0.06 g, 0.19 mmol) are placed in dichloromethane (1 mL) and 50% aqueous NaOH (0.03 mL) and stirred for 4 h. The mixture is diluted with water and is extracted with dichloromethane (2×20 mL). The combined organic extracts are dried (MgSO4) and are evaporated. The residue is purified by flash chromatography (silica gel, 98:2 dichloromethane/methanol) to provide the intermediate title compound as a colorless oil (0.05 g, 33%).

Workup

  1. extractionis extracted with dichloromethane (2×20 mL)
  2. dry with materialThe combined organic extracts are dried (MgSO4)
  3. customare evaporated
  4. customThe residue is purified by flash chromatography (silica gel, 98:2 dichloromethane/methanol)

Sources & evidence

ORD record
ord-a172bc08fb7d400e8ae0e97920553fde
Source dataset
uspto-grants-2009_11
Patent number
US07612075B2

Reaction notes

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