2,3-Dichloropyrazine → HCID 59351251, compound

HRID 887438Notes

Reaction equation

HRID 887438 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-8b31b83ffbac47e58bd39397f721d987
Source dataset
uspto-grants-2012_08
Patent number
US08247418B2

Reaction notes

Loading…