Lithium borohydride → HCID 67274399, compound

HRID 1696766Notes

Reaction equation

HRID 1696766 reaction equation
C[O:2][C:3]([C:5]1[CH:10]=[C:9]([S:11][CH3:12])[CH:8]=[C:7]([NH2:13])[N:6]=1)=O.[BH4-].[Li+]>O1CCCC1>[NH2:13][C:7]1[N:6]=[C:5]([CH2:3][OH:2])[CH:10]=[C:9]([S:11][CH3:12])[CH:8]=1

Participants

4

Reactant 2

HCID 4148881Lithium borohydrideHCID 67274196HCID 67274196, compound

Product 1

HCID 67274399HCID 67274399, compoundYield 82.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 0.198 g 6-amino-4-methylsulfanyl-pyridine-2-carboxylic acid methyl ester in 4 ml tetrahydrofuran was added 0.044 g lithiumborohydride and the mixture was stirred at room temperature for 3 h. The reaction mixture was partitioned between ethyl acetate and brine. The phases were separated and the organic phase was purified by chromatography on silica gel with ethyl acetate to ethyl acetate:methanol=9:1. to yield 0.14 g of the title compound as beige crystals. MS (ISP): 171.1 [M+H]+.

Workup

  1. customThe reaction mixture was partitioned between ethyl acetate and brine
  2. customThe phases were separated
  3. customthe organic phase was purified by chromatography on silica gel with ethyl acetate to ethyl acetate

Sources & evidence

ORD record
ord-d4af3558c7a340ca82b531cdd57d0aa1
Source dataset
uspto-grants-2012_04
Patent number
US08163778B2

Reaction notes

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