Hydrochloric Acid → (4-Methoxy-6-methylpyrimidin-2-YL)methanamine

HRID 2413080Notes

Reaction equation

HRID 2413080 reaction equation
[C:1]([C:3]1[N:8]=[C:7]([CH3:9])[CH:6]=[C:5]([O:10][CH3:11])[N:4]=1)#[N:2].Cl>[Pd].CO>[NH2:2][CH2:1][C:3]1[N:8]=[C:7]([CH3:9])[CH:6]=[C:5]([O:10][CH3:11])[N:4]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 123850914-Methoxy-6-methylpyrimidine-2-carbonitrile

Product 1

HCID 13392683(4-Methoxy-6-methylpyrimidin-2-YL)methanamineYield 39.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 4.4 g of the product from Example 8, 0.35 g 10% palladium-on-carbon catalyst, and 1.5 ml of concentrated hydrochloric acid in 70 ml methanol was shaken under an atmosphere of hydrogen at 46 p.s.i. on a Parr Hydrogenation Apparatus. After 31/2 hours, the solution was filtered through a pad of Celite and the filtrate was concentrated in vacuo. The resulting solid was taken up in water and the aqueous layer was washed with several small portions of ether. Adjustment to pH 13 followed by extraction with methylene chloride, drying, and evaporation of the organic layer gave 1.8 g of the title compound as a light yellowish-orange oil.

Workup

  1. filtrationAfter 31/2 hours, the solution was filtered through a pad of Celite
  2. concentrationthe filtrate was concentrated in vacuo
  3. washthe aqueous layer was washed with several small portions of ether
  4. extractionfollowed by extraction with methylene chloride
  5. customdrying
  6. customevaporation of the organic layer

Sources & evidence

ORD record
ord-205768a1d9714eb6a3ba38830ef17349
Source dataset
uspto-grants-1985_01
Patent number
US04496392

Reaction notes

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