Triethylamine → HCID 14116981, compound

HRID 980138Notes

Reaction equation

HRID 980138 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=[CH:5][C:4]=1[C:11]1[N:12]=[C:13]2[CH:18]=[CH:17][N:16](Cl)[CH2:15][N:14]2[CH:20]=1.[H][H].C(N(CC)CC)C>C(OCC)(=O)C.[Pd]>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=[CH:5][C:4]=1[C:11]1[N:12]=[C:13]2[CH:18]=[CH:17][N:16]=[CH:15][N:14]2[CH:20]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 20222191HCID 20222191, compoundHCID 178418361HCID 178418361, compound2×

Product 1

HCID 14116981HCID 14116981, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 3 g. of 2-(2,4-dimethoxyphenyl)-6-chloro-imidazo[1,2-c]pyrimidine (free base) in ethyl acetate was treated with 1 g. of 5% palladium-on-carbon and subjected to hydrogenation until hydrogen uptake ceased. Two grams of triethylamine were added and hydrogenation was continued. When hydrogen uptake ceased, the catalyst was removed by filtration, and the ethyl acetate solution was washed with 300 ml. of a saturated sodium chloride solution. The organic solution was evaporated in vacuo, and the resulting residue was crystallized from ethyl acetate/ether to give 1.2 g. of the title product, M+ =255.

Workup

  1. customthe catalyst was removed by filtration
  2. washthe ethyl acetate solution was washed with 300 ml
  3. customThe organic solution was evaporated in vacuo
  4. customthe resulting residue was crystallized from ethyl acetate/ether
  5. customto give 1.2 g

Sources & evidence

ORD record
ord-4d528af91a5e4405ae8c525410e38935
Source dataset
uspto-grants-1987_01
Patent number
US04636502

Reaction notes

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