2,3-Dichloropyrazine → 4-(3-Chloropyrazin-2-YL)tetrahydro-2H-pyran-4-carbonitrile

HRID 887436Notes

Reaction equation

HRID 887436 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]#[N: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]#[N: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 11815837Oxane-4-carbonitrile

Product 1

HCID 593513054-(3-Chloropyrazin-2-YL)tetrahydro-2H-pyran-4-carbonitrile

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 2,3-dichloropyrazine (1.219 g, 8.18 mmol) and tetrahydro-2H-pyran-4-carbonitrile (1 g, 9.00 mmol) in Toluene (16.36 mL) at room temperature was added LiHMDS (18.00 mL, 18.00 mmol) dropwise. The reaction mixture was stirred overnight at room temperature. Reaction was quenched with saturated NH4Cl and extracted with EtOAc. Two purifications with Biotage (0-10% MeOH/DCM & 0-100% EtOAc/Hexane) were conducted to isolate product.

Workup

  1. customReaction
  2. customwas quenched with saturated NH4Cl
  3. extractionextracted with EtOAc
  4. customto isolate product

Sources & evidence

ORD record
ord-83e76b3b94bc47a284ae1ed2a0449461
Source dataset
uspto-grants-2012_08
Patent number
US08247418B2

Reaction notes

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