4-((S)-2-hydroxy-propylamino)-2-methylsulfanyl pyrimidine-5-methanol → 4-((S)-2-hydroxy-propylamino)-2-methylsulfanyl-pyrimidine-5-carbaldehyde

HRID 2353305Notes

Reaction equation

HRID 2353305 reaction equation
[OH:1][C@@H:2]([CH3:15])[CH2:3][NH:4][C:5]1[C:10]([CH2:11][OH:12])=[CH:9][N:8]=[C:7]([S:13][CH3:14])[N:6]=1>[O-2].[O-2].[Mn+4].ClCCl>[OH:1][C@@H:2]([CH3:15])[CH2:3][NH:4][C:5]1[C:10]([CH:11]=[O:12])=[CH:9][N:8]=[C:7]([S:13][CH3:14])[N:6]=1

Participants

4

Reactant 1

HCID 596814384-((S)-2-hydroxy-propylamino)-2-methylsulfanyl pyrimidine-5-methanol

Product 1

HCID 596814334-((S)-2-hydroxy-propylamino)-2-methylsulfanyl-pyrimidine-5-carbaldehydeYield 72.6%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

4-((S)-2-hydroxy-propylamino)-2-methylsulfanyl pyrimidine-5-methanol (26 g, 100 mmol) and 1 L of dichloromethane were combined with stirring and treated with manganese dioxide (102 g, 1 mol). The resulting suspension was stirred for 24 hours and then filtered through celite. The filter residue was washed with dichloromethane (100 mL) and the combined filtrate and washings were evaporated under reduced pressure to give 16.5 g of the 4-((S)-2-hydroxy-propylamino)-2-methylsulfanyl-pyrimidine-5-carbaldehyde as a white solid.

Workup

  1. stirringThe resulting suspension was stirred for 24 hours
  2. filtrationfiltered through celite
  3. washThe filter residue was washed with dichloromethane (100 mL)
  4. customthe combined filtrate and washings were evaporated under reduced pressure

Sources & evidence

ORD record
ord-2cacce34121d4f1fbb7b6077cb8c889b
Source dataset
uspto-grants-2010_07
Patent number
US07750016B2

Reaction notes

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