2,3-Dichloropyrazine → HCID 59351251, compound

HRID 555851Notes

Reaction equation

HRID 555851 reaction equation
Cl[C:2]1[C:7]([Cl:8])=[N:6][CH:5]=[CH:4][N:3]=1.[O:9]1[CH2:14][CH2:13][CH:12]([C:15]([O:17][CH3:18])=[O:16])[CH2:11][CH2:10]1.[Li+].C[Si]([N-][Si](C)(C)C)(C)C>C1(C)C=CC=CC=1>[Cl:8][C:7]1[C:2]([C:12]2([C:15]([O:17][CH3:18])=[O:16])[CH2:13][CH2:14][O:9][CH2:10][CH2:11]2)=[N:3][CH:4]=[CH:5][N:6]=1

Participants

5

Reactant 3

HCID 785752,3-DichloropyrazineHCID 2733832Lithium HexamethyldisilazideHCID 27735202H-Pyran-4-carboxylic acid, tetrahydro-, methyl ester

Product 1

HCID 59351251HCID 59351251, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 2,3-dichloropyrazine (1.45 g, 9.73 mmol) and methyl tetrahydro-2H-pyran-4-carboxylate (2.60 mL, 19.47 mmol) in Toluene (19.47 mL) at room temperature was added LiHMDS (19.47 mL, 19.47 mmol, 1M solution) dropwise. After overnight room temperature stirring, reaction was quenched with saturated NH4Cl solution and extracted with EtOAc. Purification by Biotage (0-10% MeOH/DCM) produced product.

Workup

  1. customreaction
  2. customwas quenched with saturated NH4Cl solution
  3. extractionextracted with EtOAc
  4. customPurification by Biotage (0-10% MeOH/DCM)
  5. customproduced product

Sources & evidence

ORD record
ord-75f82819422b46fc8b05a967881a250b
Source dataset
uspto-grants-2011_11
Patent number
US08053438B2

Reaction notes

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