Phenylacetyl chloride → N-[4-(dimethylamino)-6-(4-toluidino)-2-pyrimidinyl]-2-phenylacetamide

HRID 1352896Notes

Reaction equation

HRID 1352896 reaction equation
[CH3:1][N:2]([CH3:18])[C:3]1[CH:8]=[C:7]([NH:9][C:10]2[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][CH:11]=2)[N:6]=[C:5]([NH2:17])[N:4]=1.[C:19]1([CH2:25][C:26](Cl)=[O:27])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C(N(CC)CC)C>C(Cl)Cl>[CH3:18][N:2]([CH3:1])[C:3]1[CH:8]=[C:7]([NH:9][C:10]2[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][CH:11]=2)[N:6]=[C:5]([NH:17][C:26](=[O:27])[CH2:25][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[N:4]=1

Participants

5

Reactant 3

HCID 7679Phenylacetyl chlorideHCID 8471TriethylamineHCID 68563652N4,N4-dimethyl-N6-(4-methylphenyl)-2,4,6-pyrimidinetriamine

Product 1

HCID 21101364N-[4-(dimethylamino)-6-(4-toluidino)-2-pyrimidinyl]-2-phenylacetamideYield 33.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of N4,N4-dimethyl-N6-(4-methylphenyl)-2,4,6-pyrimidinetriamine (122 mg, 0.50 mmol), phenylacetyl chloride (84 mg, 0.55 mmol), and triethylamine (100 mg, 1.00 mmol) in CH2Cl2 was stirred at room temperature for 16 h. The crude product was concentrated in vacuo and treated with saturated NaHCO3 (50 mL) and extracted with CH2Cl2 (3×50 mL). The organic layer was washed with brine (2×100 mL), dried over Na2SO4, filtered, and concentrated in vacuo. The crude product was purified by preparative TLC using hexane/EtOAc (1:3), giving the desired product (60 mg, 33%).

Workup

  1. concentrationThe crude product was concentrated in vacuo
  2. additiontreated with saturated NaHCO3 (50 mL)
  3. extractionextracted with CH2Cl2 (3×50 mL)
  4. washThe organic layer was washed with brine (2×100 mL)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude product was purified by preparative TLC

Sources & evidence

ORD record
ord-59c405fc0b934ae49e718ff2fcb5c0cd
Source dataset
uspto-grants-2007_05
Patent number
US07220775B2

Reaction notes

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