Phenylacetyl chloride → HCID 59508992, compound

HRID 1020076Notes

Reaction equation

HRID 1020076 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[N:14]=[CH:13][N:12]=[C:11]([NH2:15])[CH:10]=1.CCN(CC)CC.[C:23]1([CH2:29][C:30](Cl)=[O:31])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>C1COCC1>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[N:14]=[CH:13][N:12]=[C:11]([NH:15][C:30](=[O:31])[CH2:29][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:10]=1

Participants

5

Reactant 3

HCID 7679Phenylacetyl chlorideHCID 8471TriethylamineHCID 497584396-(2-Methoxyphenyl)pyrimidin-4-amine

Product 1

HCID 59508992HCID 59508992, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 6-(2-methoxy-phenyl)-pyrimidin-4-ylamine (XXIV) (0.15 g, 0.74 mmol) in THF (10 ml) was added NEt3 (0.210 ml, 1.49 mmol) under an atmosphere of nitrogen at ice bath temperature, followed by phenyl acetyl chloride (XLVI) (0.819 mmol) at the same temperature. The reaction mixture was stirred for 1 hour at 0° C. and then brought to room temperature and stirred for another hour. Usual work up as described above followed by column chromatographic purification over silica gel (30% ethyl acetate/hexane) yielded N-[6-(2-methoxy-phenyl)-pyrimidin-4-yl]-2-phenyl-acetamide.

Workup

  1. custombrought to room temperature
  2. stirringstirred for another hour
  3. customabove followed by column chromatographic purification over silica gel (30% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-c8a3057562bf48b4826e532f629abee9
Source dataset
uspto-grants-2014_05
Patent number
US08716296B2

Reaction notes

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