Methanol → HCID 18966212, compound

HRID 2226092Notes

Reaction equation

HRID 2226092 reaction equation
[CH3:1]O.[CH3:3][O:4][C:5]1[CH:10]=[C:9]([O:11][CH3:12])[N:8]=[C:7]([S:13][C:14](C)([CH2:17][CH3:18])[CH:15]=[O:16])[N:6]=1.B.[Na]>O>[CH3:12][O:11][C:9]1[CH:10]=[C:5]([O:4][CH3:3])[N:6]=[C:7]([S:13][CH:14]([CH:17]([CH3:18])[CH3:1])[CH2:15][OH:16])[N:8]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 86748130HCID 86748130, compoundHCID 178418435HCID 178418435, compound

Product 1

HCID 18966212HCID 18966212, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a methanol solution of 2-(4,6-dimethoxy-2-pyrimidinylthio)-methyl butyraldehyde (1.5 g) was added sodium boron hydride (0.2 g), followed by a five-minute stirring at room temperature. Water was then added to the reaction liquid, followed by extraction with ethyl acetate, water-washing of the resulting organic layer and drying thereof in that order. After the removal of the drying agent from the reaction product under filtration, followed by separation of ethyl acetate under reduced pressure distillation, there was obtained an oily substance that was then purified by silica gel column chromatography to obtain the desired 2-(4,6-dimethoxy-2-pyrimidinylthio)-3-methylbutanol (1.3 g) n20D 1.5445.

Workup

  1. customfollowed by a five-minute stirring at room temperature
  2. extractionfollowed by extraction with ethyl acetate, water-
  3. washwashing of the resulting organic layer
  4. customdrying
  5. customAfter the removal of the drying agent from the reaction product
  6. filtrationunder filtration
  7. customfollowed by separation of ethyl acetate under reduced pressure distillation
  8. customthere was obtained an oily substance that
  9. customwas then purified by silica gel column chromatography

Sources & evidence

ORD record
ord-ea23cb10784a48abb59b1ea60e219d9f
Source dataset
uspto-grants-1994_09
Patent number
US05346880

Reaction notes

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