Water → HCID 22648761, compound

HRID 393165Notes

Reaction equation

HRID 393165 reaction equation
Br[C:2]1[C:3]([S:8][CH3:9])=[N:4][CH:5]=[N:6][CH:7]=1.CCC[CH2:13][CH2:14][CH3:15].O.[O:17]1CCC[CH2:18]1>>[OH:17][CH:18]([C:2]1[C:3]([S:8][CH3:9])=[N:4][CH:5]=[N:6][CH:7]=1)[CH:14]([CH3:13])[CH3:15]

Participants

5

Reactant 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 8058HexaneHCID 122700805-bromo-4-methylthiopyrimidine

Product 1

HCID 22648761HCID 22648761, compoundYield 28%

Conditions

Temperature
-60 °C

Procedure

10.6 g (52 mmol) of 5-bromo-4-methylthiopyrimidine was dissolved in 100 ml of tetrahydrofuran, and at −60° C., 36 ml of a n-butylithium hexane solution (1.6 mol/l) was dropwise added. After stirring at −60° C. for 30 minutes, 4.1 g (57 mmol) of isobutylaldehyde was dropwise added and further reacted for 1 hour. The reaction solution was poured into water and extracted with ethyl acetate. The obtained organic layer was washed with water and then dried over anhydrous magnesium sulfate. Ethyl acetate was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (developing solvent/n-hexane:ethyl acetate=3:2) to obtain 2.9 g (yield: 28%) of 5-(1-hydroxy-2-methylpropyl)-4-methylthiopyrimidine as slightly yellow crystals (melting point: 123-127° C.).

Workup

  1. customfurther reacted for 1 hour
  2. extractionextracted with ethyl acetate
  3. washThe obtained organic layer was washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationEthyl acetate was distilled off under reduced pressure
  6. customthe residue was purified by silica gel column chromatography (developing solvent/n-hexane:ethyl acetate=3:2)

Sources & evidence

ORD record
ord-2378c47ddfc0440bb39b47eead57cb9c
Source dataset
uspto-grants-2004_10
Patent number
US06806230B1

Reaction notes

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