Water → HCID 11744819, compound

HRID 1199592Notes

Reaction equation

HRID 1199592 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-154cc6cdda9441a9ac3021bb0c290a5d
Source dataset
uspto-grants-1990_02
Patent number
US04902332

Reaction notes

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