Diisobutylaluminum hydride → HCID 58574335, compound

HRID 1619384Notes

Reaction equation

HRID 1619384 reaction equation
[Br:1][C:2]1[CH:16]=[CH:15][N:5]2[C:6](=[O:14])[C:7]([C:10](OC)=[O:11])=[CH:8][N:9]=[C:4]2[CH:3]=1.CC(C[AlH]CC(C)C)C>C1COCC1>[Br:1][C:2]1[CH:16]=[CH:15][N:5]2[C:6](=[O:14])[C:7]([CH2:10][OH:11])=[CH:8][N:9]=[C:4]2[CH:3]=1

Participants

4

Reactant 2

HCID 14487Diisobutylaluminum hydrideHCID 58574864HCID 58574864, compound

Product 1

HCID 58574335HCID 58574335, compoundYield 16.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 8-bromo-4-oxo-4H-pyrido[1,2-a]pyrimidine-3-carboxylate (1 g, 3.5 mmol, 1 equiv) in anhydrous THF (25 mL) was added DIBAL-H (5 mL) at 0° C. dropwise. After stirring for 1 h, the reaction mixture was quenched with saturated NH4Cl. The solution was extracted with ethyl acetate (3×150 mL). The combined organic layers were dried over Na2SO4 and concentrated to give the crude product. The crude was purified by column chromatography to give 145 mg of the desired product. MS (ESI): 255, 257 (MH+).

Workup

  1. customthe reaction mixture was quenched with saturated NH4Cl
  2. extractionThe solution was extracted with ethyl acetate (3×150 mL)
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. concentrationconcentrated
  5. customto give the crude product
  6. customThe crude was purified by column chromatography

Sources & evidence

ORD record
ord-2ff5f845aec9474f8c93eab479057b30
Source dataset
uspto-grants-2014_07
Patent number
US08772301B2

Reaction notes

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