Formic Acid → 4-Amino-2-methylpyrimidine-5-carbaldehyde

HRID 1679889Notes

Reaction equation

HRID 1679889 reaction equation
[NH2:1][C:2]1[C:7]([C:8]#N)=[CH:6][N:5]=[C:4]([CH3:10])[N:3]=1.C(O)=[O:12].[H][H]>[Ni].O>[NH2:1][C:2]1[C:7]([CH:8]=[O:12])=[CH:6][N:5]=[C:4]([CH3:10])[N:3]=1

Participants

6

Reactant 3

HCID 284Formic AcidHCID 696824-Amino-2-methylpyrimidine-5-carbonitrileHCID 178418361HCID 178418361, compound

Product 1

HCID 129047264-Amino-2-methylpyrimidine-5-carbaldehyde

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 962WaterSolvent

Procedure

A mixture of 76.5 g of 4-amino-2-methylpyrimidine-5-carbonitrile, 380 ml of 97% formic acid, 380 ml of water, and 8 g of Raney nickel catalyst is treated in a Parr pressure apparatus with hydrogen gas at an initial pressure of 51 psi at room temperature for 2.75 hours. The catalyst is removed by filtration and the filtrate is treated with 47.5 ml of concentrated hydrochloric acid and evaporated at reduced pressure. The residue is dissolved in hot water, treated with charcoal and filtered. Neutralization of the filtrate with concentrated ammonium hydroxide precipitates the product which is then collected by filtration and washed with water. Recrystallization from ethanol gives 37.9 g of 4-amino-2-methylpyrimidine-5-carboxaldehyde, mp 191°-192.5° C.

Workup

  1. customThe catalyst is removed by filtration
  2. additionthe filtrate is treated with 47.5 ml of concentrated hydrochloric acid
  3. customevaporated at reduced pressure
  4. dissolutionThe residue is dissolved in hot water
  5. additiontreated with charcoal
  6. filtrationfiltered
  7. customNeutralization of the filtrate with concentrated ammonium hydroxide precipitates the product which
  8. filtrationis then collected by filtration
  9. washwashed with water
  10. customRecrystallization from ethanol

Sources & evidence

ORD record
ord-e5f874027d324deab40d70263b0c7c01
Source dataset
uspto-grants-1981_06
Patent number
US04271164

Reaction notes

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