Diisobutylaluminum hydride → HCID 57839048, compound

HRID 732952Notes

Reaction equation

HRID 732952 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[C:14]([C:15]([O-])=[O:16])=[C:13]([CH3:18])[N:12]=[C:11]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[N:10]=1.CC(C[AlH]CC(C)C)C>C1COCC1>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[C:14]([CH2:15][OH:16])=[C:13]([CH3:18])[N:12]=[C:11]([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[N:10]=1

Participants

4

Reactant 2

HCID 14487Diisobutylaluminum hydrideHCID 86606140HCID 86606140, compound

Product 1

HCID 57839048HCID 57839048, compoundYield 108.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 4-(2,4-dichlorophenyl)-6-methyl-2-phenylpyrimidine-5-carboxylate (75 mg, 0.2 mmol) in THF (6 mL) was added DIBAL (0.4 mL, 1.5 M in PhCH3, 0.6 mmol). The reaction was kept for 1 hr and was quenched by saturated aqueous potassium sodium tartrate solution (5 mL). The reaction was diluted with EtOAc (10 mL) and the organic layer was washed with 1N NaOH (10 mL), saturated Na2CO3 solution (10 mL) and brine (10 mL), dried (MgSO4), filtered and concentrated under reduced pressure to give the crude product as a white solid (75 mg). The crude reaction product was moved onto next step without further purification.

Workup

  1. customwas quenched by saturated aqueous potassium sodium tartrate solution (5 mL)
  2. additionThe reaction was diluted with EtOAc (10 mL)
  3. washthe organic layer was washed with 1N NaOH (10 mL), saturated Na2CO3 solution (10 mL) and brine (10 mL)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-4ba9534255994870b98be723ad988160
Source dataset
uspto-grants-2009_09
Patent number
US07589088B2

Reaction notes

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