Tetrahydrofuran → HCID 14988419, compound

HRID 2051504Notes

Reaction equation

HRID 2051504 reaction equation
C(C1[CH:4]=[N:5][C:6]([NH:9][C:10](=[O:14])[CH:11]([CH3:13])[CH3:12])=[N:7]C=1)=C.[Br:15][CH:16]1CC(=O)NC1=O.[O:23]1[CH2:27][CH2:26][CH2:25]C1>O>[C:10]([NH:9][C:6]1[N:7]=[CH:25][C:26]([CH:27]([OH:23])[CH2:16][Br:15])=[CH:4][N:5]=1)(=[O:14])[CH:11]([CH3:13])[CH3:12]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 38309BromosuccinimideHCID 14988418HCID 14988418, compound

Product 1

HCID 14988419HCID 14988419, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 764 mg of 5-ethenyl-2-(isobutyramido)pyrimidine in a mixture of 3 ml of water and 7 ml of tetrahydrofuran, 710 mg of N bromosuccinimide was added. The reaction mixture was stirred at room temperature for 18 hours and then partially concentrated under reduced pressure. To the aqueous residue 25 ml of methylene chloride was added and the layers separated. The aqueous layer was further extracted with methylene chloride (20 ml). The combined organic extracts were washed with 20 ml of water and then dried over anhydrous magnesium sulfate. Concentration afforded 977 mg of a glassy product. This material was chromatographed on silica gel (95:5 methylene chloride:methanol) to give 491 mg of pure bromohydrin.

Workup

  1. additionwas added
  2. concentrationpartially concentrated under reduced pressure
  3. additionTo the aqueous residue 25 ml of methylene chloride was added
  4. customthe layers separated
  5. extractionThe aqueous layer was further extracted with methylene chloride (20 ml)
  6. washThe combined organic extracts were washed with 20 ml of water
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationConcentration

Sources & evidence

ORD record
ord-658cdcd885ab40588ea31a72e0b349b7
Source dataset
uspto-grants-1991_05
Patent number
US05019578

Reaction notes

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