Ammonium Chloride → HCID 58426988, compound

HRID 2176449Notes

Reaction equation

HRID 2176449 reaction equation
[CH:1]([C@@H:4]1[C:9]([O:10][CH3:11])=[N:8][CH2:7][C:6]([O:12][CH3:13])=[N:5]1)([CH3:3])[CH3:2].[Cl:14][CH2:15][Si:16]([CH2:19]Cl)([CH3:18])[CH3:17].C([Li])CCC.[Cl-].[NH4+]>C1COCC1>[Cl:14][CH2:15][Si:16]([CH2:19][C@H:7]1[C:6]([O:12][CH3:13])=[N:5][C@H:4]([CH:1]([CH3:3])[CH3:2])[C:9]([O:10][CH3:11])=[N:8]1)([CH3:18])[CH3:17]

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 76212Bis(chloromethyl)dimethylsilaneHCID 736066(R)-2,5-Dihydro-3,6-dimethoxy-2-isopropylpyrazineHCID 178418339Butyllithium

Product 1

HCID 58426988HCID 58426988, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (R)-2-isopropyl-3,6-dimethoxy-2,5-dihydro-pyrazine (7.0 g, 38 mmol), bis(chloromethyl)dimethylsilane (6.0 g, 38 mmol) in THF (150 mL) was added n-butyl-lithium (20 mL, 50 mmol) at −65 to −75° C. dropwise. The mixture was allowed to gradually warm to RT overnight. An ammonium chloride solution at 0° C. was added and the reaction mixture was extracted with EtOAc. The organic layer was washed with water and brine, dried over Na2SO4, concentrated, and purified by silica gel chromatography (2% EtOAc in petroleum ether) to give the title intermediate (5 g, 44% yield) as a clear oil 1H NMR: (MeOD, 400 MHz) δ(ppm): 4.15 (m, 1H), 3.99 (m, 1H), 3.72 (m, 6H), 2.95 (m, 2H), 2.30 (m, 1H), 1.45 (m, 1H), 1.08 (m, 4H), 0.75 (m, 3H), 0.26 (s, 6H).

Workup

  1. extractionthe reaction mixture was extracted with EtOAc
  2. washThe organic layer was washed with water and brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. custompurified by silica gel chromatography (2% EtOAc in petroleum ether)

Sources & evidence

ORD record
ord-6859434313574eb09b9f0bcb6f4fd1a4
Source dataset
uspto-grants-2015_06
Patent number
US09066944B2

Reaction notes

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