Dimethylformamide dimethyl acetal → 4-(Dimethoxymethyl)-N-methylpyrimidin-2-amine

HRID 552115Notes

Reaction equation

HRID 552115 reaction equation
[CH3:1][O:2][CH:3]([O:7][CH3:8])N(C)C.[CH3:9][C:10]([CH:12](OC)OC)=O.[O-]CC.[Na+].Cl.[CH3:22][NH:23][C:24]([NH2:26])=[NH:25]>C(O)C>[CH3:8][O:7][CH:3]([O:2][CH3:1])[C:12]1[CH:10]=[CH:9][N:26]=[C:24]([NH:23][CH3:22])[N:25]=1

Participants

6

Reactant 4

HCID 78373Dimethylformamide dimethyl acetalHCID 80650Pyruvic aldehyde dimethyl acetalHCID 2723922Sodium ethoxideHCID 178485118HCID 178485118, compound

Product 1

HCID 178400144-(Dimethoxymethyl)-N-methylpyrimidin-2-amine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 5.5 mL (41 mmol, 1.0 eq.) of dimethylformamide dimethyl acetal and 5.0 mL (41 mmol, 1.0 eq.) of pyruvic aldehyde dimethyl acetal was heated at 100° C. for 16 h. Methanol was removed in vacuo to afford a brown oil. To a solution of 15 mL of sodium ethoxide (21% in ethanol, 41 mmol, 1.0 eq.) was added 4.5 g (41 mmol, 1.0 eq.) of methyl guanidine HCl. The mixture was stirred for 10 min before a solution of the above described oil in 15 mL anhydrous ethanol was added. The mixture was heated to reflux for 24 h, allowed to cool to room temperature and filtered. The solvent was removed in vacuo to afford 2-methylaminopyrimidine-4-carboxaldehyde dimethyl acetal (I-10) as a dark brown oil which was used in the next step without further purification

Workup

  1. customMethanol was removed in vacuo
  2. customto afford a brown oil
  3. additionwas added
  4. temperatureThe mixture was heated
  5. temperatureto reflux for 24 h
  6. filtrationfiltered
  7. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-7c603a19d1394def81dc14776aa0b72d
Source dataset
uspto-grants-2011_05
Patent number
US07951803B2

Reaction notes

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