Tetrahydro-4H-pyran-4-one → 4-(3-Fluoropyrazin-2-YL)tetrahydro-2H-pyran-4-OL

HRID 555855Notes

Reaction equation

HRID 555855 reaction equation
[F:1][C:2]1[C:7](I)=[N:6][CH:5]=[CH:4][N:3]=1.[O:9]1[CH2:14][CH2:13][C:12](=[O:15])[CH2:11][CH2:10]1>C1COCC1>[F:1][C:2]1[C:7]([C:12]2([OH:15])[CH2:13][CH2:14][O:9][CH2:10][CH2:11]2)=[N:6][CH:5]=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 121599Tetrahydro-4H-pyran-4-oneHCID 153696932-Fluoro-3-iodopyrazine

Product 1

HCID 593512304-(3-Fluoropyrazin-2-YL)tetrahydro-2H-pyran-4-OL

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 2-fluoro-3-iodopyrazine (1 g, 4.46 mmol) in THF (4.46 mL) at 0° C. was added isopropylmagnesium chloride lithium chloride complex, 1.0M solution in THF (4.87 mL, 4.46 mmol). The resulting mixture was stirred for 5 min before addition of dihydro-2H-pyran-4(3H)-one (0.410 mL, 4.46 mmol). Reaction mixture was allowed to warm to room temperature and stirred overnight. Purification by Biotage (0-100% EtOAc/hexane) produced the product.

Workup

  1. customReaction mixture
  2. customPurification by Biotage (0-100% EtOAc/hexane)
  3. customproduced the product

Sources & evidence

ORD record
ord-c49931cb99d740c18e4e026580dd6c21
Source dataset
uspto-grants-2011_11
Patent number
US08053438B2

Reaction notes

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