4-chloro-5,6-dimethylpyrimidin-2-amine → 4,5-dimethylpyrimidin-2-amine

HRID 250040Notes

Reaction equation

HRID 250040 reaction equation
Cl[C:2]1[C:7]([CH3:8])=[C:6]([CH3:9])[N:5]=[C:4]([NH2:10])[N:3]=1>N.CO.[Pd]>[CH3:9][C:6]1[C:7]([CH3:8])=[CH:2][N:3]=[C:4]([NH2:10])[N:5]=1

Participants

5

Reactant 1

HCID 2486554-chloro-5,6-dimethylpyrimidin-2-amine

Product 1

HCID 2312904,5-dimethylpyrimidin-2-amineYield 115.3%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 222AmmoniaSolventHCID 887MethanolSolvent

Procedure

A solution of 4-chloro-5,6-dimethylpyrimidin-2-amine (0.35 g, 2.22 mmol) in 2M ammonia in methanol (100 ml) was flushed with nitrogen and palladium on carbon (0.035 g, 0.33 mmol) was added, flushed with nitrogen and the reaction was hydrogenated at 1 atm, ambient temperature for 18 h. The reaction mixture was flushed with nitrogen and filtered through celite and the celite pad washed with methanol. The filtrate was evaporated to dryness in vacuo to afford 4,5-dimethylpyrimidin-2-amine (0.35 g, 2.56 mmol, 90% yield) which was used without further purification. 1H NMR (400 MHz, DMSO-d6) δ ppm 7.89 (1 H, s), 6.19 (2 H, s), 2.18 (3 H, s), 1.99 (3 H, s). MS (LC/MS) R.T.=0.56; [M+H]+=124.20.

Workup

  1. additionwas added
  2. customflushed with nitrogen
  3. customThe reaction mixture was flushed with nitrogen
  4. filtrationfiltered through celite
  5. washthe celite pad washed with methanol
  6. customThe filtrate was evaporated to dryness in vacuo

Sources & evidence

ORD record
ord-a7938e16648e4662b9ef259f37665f9f
Source dataset
uspto-grants-2011_01
Patent number
US07863291B2

Reaction notes

Loading…