Methyl 2-methoxy-6-methylpyrimidine-4-carboxylate → 2-Methoxy-6-methylpyrimidine-4-carbaldehyde

HRID 2264159Notes

Reaction equation

HRID 2264159 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[C:7]([C:9](OC)=[O:10])[CH:6]=[C:5]([CH3:13])[N:4]=1.[H-].C([Al+]CC(C)C)C(C)C>C1(C)C=CC=CC=1.ClCCl>[CH3:1][O:2][C:3]1[N:8]=[C:7]([CH:9]=[O:10])[CH:6]=[C:5]([CH3:13])[N:4]=1

Participants

5

Reactant 2

HCID 19018471Methyl 2-methoxy-6-methylpyrimidine-4-carboxylateHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 552623542-Methoxy-6-methylpyrimidine-4-carbaldehyde

Reagents, catalysts & solvents 2

HCID 1140TolueneSolvent2×HCID 6344DichloromethaneSolvent

Procedure

To an cooled solution (−78° C. internal temp) of 0.5 g of methyl 2-methoxy-6-methylpyrimidine-4-carboxylate in 15 mL of toluene and 15 mL of dichloromethane was added 6 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 an resin and was used without further purification: MS (m+1)=153.1 and 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 an resin
  4. customwas used without further purification

Sources & evidence

ORD record
ord-801e5e0b196a4001abb07374a0d2c4bc
Source dataset
uspto-grants-2010_12
Patent number
US07855201B2

Reaction notes

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