Ethanol → 3-(4-Ethylamino-2-phenylamino-pyrimidin-5-yl)propionic acid ethyl ester

HRID 2300067Notes

Reaction equation

HRID 2300067 reaction equation
[CH2:1]([NH:3][C:4]1[C:9]([CH:10]=[CH:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:8][N:7]=[C:6]([NH:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[N:5]=1)[CH3:2].C(O)C>[Pd].O1CCCC1>[CH2:15]([O:14][C:12](=[O:13])[CH2:11][CH2:10][C:9]1[C:4]([NH:3][CH2:1][CH3:2])=[N:5][C:6]([NH:17][C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)=[N:7][CH:8]=1)[CH3:16]

Participants

5

Reactant 2

HCID 702EthanolHCID 54014983Ethyl 3-(4-ethylamino-2-phenylamino pyrimidin-5-yl)acrylate

Product 1

HCID 542432123-(4-Ethylamino-2-phenylamino-pyrimidin-5-yl)propionic acid ethyl esterYield 47.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of ethyl 3-(4-ethylamino-2-phenylamino-pyrimidin-5-yl)acrylate (152 mg, 0.48 mmol) and 5% palladium on carbon in a solvent mixture of ethanol and tetrahydrofuran was hydrogenated under pressure. The catalyst was filtered off and the filtrate concentrated. The residue was purified by flash chromatography eluting with 2:1 ethyl acetate:hexane to give 72 mg (47%) of 3-(4-ethylamino-2-phenylamino-pyrimidin-5-yl)propionic acid ethyl ester, mp 106-107° C.

Workup

  1. filtrationThe catalyst was filtered off
  2. concentrationthe filtrate concentrated
  3. customThe residue was purified by flash chromatography
  4. washeluting with 2:1 ethyl acetate

Sources & evidence

ORD record
ord-e98c2820f0474c36aded767a2e883564
Source dataset
uspto-grants-2002_12
Patent number
US06498163B1

Reaction notes

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