Water → HCID 11744819, compound

HRID 2352127Notes

Reaction equation

HRID 2352127 reaction equation
C([Li])CCC.Br[C:7]1[CH:8]=[N:9][CH:10]=[N:11][CH:12]=1.[CH:13](=[O:17])[CH:14]([CH3:16])[CH3:15].O>O1CCCC1>[CH3:15][CH:14]([CH3:16])[CH:13]([C:7]1[CH:8]=[N:9][CH:10]=[N:11][CH:12]=1)[OH:17]

Participants

6

Reactant 4

HCID 962WaterHCID 6561IsobutyraldehydeHCID 783445-BromopyrimidineHCID 178418339Butyllithium

Product 1

HCID 11744819HCID 11744819, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

To a solution of n-butyl lithium (20 ml of 2.6 M, 52 mmol) in dry tetrahydrofuran (60 ml) at -78° C., was added a cold solution of 5-bromopyrimidine (6.36 g, 40 mmol) in dry tetrahydrofuran (30 ml) over a period of 5 minutes. After 10 minutes a cold solution of iso-butyraldehyde (2.88 g, 40 mmol) in dry tetrahydrofuran (30 ml) was added dropwise. The mixture was allowed to warm to room temperature and stirred for 16 hours. The reaction mixture was poured into water and extracted with ether (2×100 ml). The organic layer was collected, washed with brine and dried over magnesium sulphate before removing the solvent. Flash chromatography (silica gel, petrol/ether elution) gave the product as a yellow oil.

Workup

  1. extractionextracted with ether (2×100 ml)
  2. customThe organic layer was collected
  3. washwashed with brine
  4. dry with materialdried over magnesium sulphate
  5. custombefore removing the solvent
  6. washFlash chromatography (silica gel, petrol/ether elution)

Sources & evidence

ORD record
ord-3596b19308224c6c8da2a833bab66d26
Source dataset
uspto-grants-1989_10
Patent number
US04875922

Reaction notes

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