Methyl 4-methoxypyrimidine-5-carboxylate → 4-Methoxypyrimidine-5-carbaldehyde

HRID 2264163Notes

Reaction equation

HRID 2264163 reaction equation
[CH3:1][O:2][C:3]1[C:8]([C:9](OC)=[O:10])=[CH:7][N:6]=[CH:5][N:4]=1.[H-].C([Al+]CC(C)C)C(C)C>ClCCl.C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[C:8]([CH:9]=[O:10])=[CH:7][N:6]=[CH:5][N:4]=1

Participants

5

Reactant 2

HCID 12828992Methyl 4-methoxypyrimidine-5-carboxylateHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 198757634-Methoxypyrimidine-5-carbaldehyde

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

To an cooled solution (−78° C. internal temp) of 0.3 g of methyl 4-methoxypyrimidine-5-carboxylate in 20 mL of dichloromethane was added 2 mL of 1 M diisobutyl aluminum hydride in toluene. After stirring 10 min the reaction was quenched with 5 mL of water, allowed to warm to room temperature and dried with 5 g of MgSO4. Concentration of the filtrate under reduced pressure gave the product as a resin and was used without further purification: MS (m+1)=171.1 (hydrate).

Workup

  1. customwas quenched with 5 mL of water
  2. dry with materialdried with 5 g of MgSO4
  3. customConcentration of the filtrate under reduced pressure gave the product as a resin
  4. customwas used without further purification

Sources & evidence

ORD record
ord-1f1112b638b44d03876167f0d5214d19
Source dataset
uspto-grants-2010_12
Patent number
US07855201B2

Reaction notes

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