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

HRID 1875906Notes

Reaction equation

HRID 1875906 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 (1H, s), 6.19 (2H, s), 2.18 (3H, s), 1.99 (3H, 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-c65081f5e2374f3c97f3b4c2641dc767
Source dataset
uspto-grants-2012_11
Patent number
US08309577B2

Reaction notes

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