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

HRID 555849Notes

Reaction equation

HRID 555849 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-b92a8efba7ce461dac88d79a9eea409b
Source dataset
uspto-grants-2011_11
Patent number
US08053438B2

Reaction notes

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