Ammonium formate → N-(2,4-Dimethoxybenzyl)pyrimidin-4-amine

HRID 1619712Notes

Reaction equation

HRID 1619712 reaction equation
Cl[C:2]1[N:7]=[CH:6][N:5]=[C:4]([NH:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][C:11]=2[O:18][CH3:19])[CH:3]=1.C([O-])=O.[NH4+]>C(O)C>[CH3:19][O:18][C:11]1[CH:12]=[C:13]([O:16][CH3:17])[CH:14]=[CH:15][C:10]=1[CH2:9][NH:8][C:4]1[CH:3]=[CH:2][N:7]=[CH:6][N:5]=1

Participants

4

Reactant 2

HCID 2723923Ammonium formateHCID 55190931HCID 55190931, compound

Product 1

HCID 63362995N-(2,4-Dimethoxybenzyl)pyrimidin-4-amineYield 97%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

6-Chloro-N-(2,4-dimethoxybenzyl)pyrimidin-4-amine (Preparation 112, 3.46 g, 12.39 mmol) was dissolved in ethanol (140 mL). The solution was degassed and then 10% palladium on carbon (0.98 g) was added followed by ammonium formate (4.55 g, 72.15 mmol) and the reaction was heated at 80° C. for 2 hours. The reaction was cooled to room temperature, filtered through pad of Celite™ and the filtrate was concentrated in vacuo. The residue was partitioned between dichloromethane (30 mL) and water (15 mL). The organic layer was separated, dried over anhydrous MgSO4, filtered and evaporated to give the title compound (2.94 g, 97%) as viscous oil.

Workup

  1. customThe solution was degassed
  2. addition10% palladium on carbon (0.98 g) was added
  3. temperatureThe reaction was cooled to room temperature
  4. filtrationfiltered through pad of Celite™
  5. concentrationthe filtrate was concentrated in vacuo
  6. customThe residue was partitioned between dichloromethane (30 mL) and water (15 mL)
  7. customThe organic layer was separated
  8. dry with materialdried over anhydrous MgSO4
  9. filtrationfiltered
  10. customevaporated

Sources & evidence

ORD record
ord-f5c571e401594ebf840393c41adefd7e
Source dataset
uspto-grants-2014_07
Patent number
US08772293B2

Reaction notes

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