Methanol → 5-chloro-1-(5-hydroxymethyl-pyrazin-2-yl)-1H-pyridin-2-one

HRID 1421729Notes

Reaction equation

HRID 1421729 reaction equation
C[O:2][C:3]([C:5]1[CH:10]=[N:9][C:8]([N:11]2[CH:16]=[C:15]([Cl:17])[CH:14]=[CH:13][C:12]2=[O:18])=[CH:7][N:6]=1)=O.CO.[BH4-].[Na+]>C(Cl)Cl>[Cl:17][C:15]1[CH:14]=[CH:13][C:12](=[O:18])[N:11]([C:8]2[CH:7]=[N:6][C:5]([CH2:3][OH:2])=[CH:10][N:9]=2)[CH:16]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 4311764Sodium borohydrideHCID 538392155-(5-chloro-2-oxo-2H-pyridin-1-yl)-pyrazine-2-carboxylic acid methyl ester

Product 1

HCID 187797445-chloro-1-(5-hydroxymethyl-pyrazin-2-yl)-1H-pyridin-2-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of the ester from step 2 (1.41 g, 5.317 mmol), in CH2Cl2 and methanol (1:1 50 ml) at 0° C. was treated with sodium borohydride (2.01 g, 53.17 mmol) and the reaction was stirred at room temperature for 18 hrs. The solvent was evaporated in vacuo and the residue was dissolved in EtOAc and sat. NaHCO3. The aqueous layer was extracted with EtOAc and the combined extracts were dried (MgSO4) and evaporated in vacuo. The residue was chromatographed (silica gel, MeOH: CH2Cl2 2:98 to 5:95 gradient elution) to afford the title compound.

Workup

  1. customThe solvent was evaporated in vacuo
  2. dissolutionthe residue was dissolved in EtOAc
  3. extractionThe aqueous layer was extracted with EtOAc
  4. dry with materialthe combined extracts were dried (MgSO4)
  5. customevaporated in vacuo
  6. customThe residue was chromatographed
  7. wash(silica gel, MeOH: CH2Cl2 2:98 to 5:95 gradient elution)

Sources & evidence

ORD record
ord-ccf385782e444f4c908b2380eeb765c8
Source dataset
uspto-grants-2000_06
Patent number
US06077853

Reaction notes

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