4-Aminobenzonitrile → 7-Acetoxy-4-(4-cyanoanilino)-6,7-dihydro-5H-cyclopenta[d]pyrimidine

HRID 579747Notes

Reaction equation

HRID 579747 reaction equation
[C:1]([O:4][CH:5]1[C:9]2[N:10]=[CH:11][N:12]=[C:13](Cl)[C:8]=2[CH2:7][CH2:6]1)(=[O:3])[CH3:2].[NH2:15][C:16]1[CH:23]=[CH:22][C:19]([C:20]#[N:21])=[CH:18][CH:17]=1>C(O)C>[C:1]([O:4][CH:5]1[C:9]2[N:10]=[CH:11][N:12]=[C:13]([NH:15][C:16]3[CH:23]=[CH:22][C:19]([C:20]#[N:21])=[CH:18][CH:17]=3)[C:8]=2[CH2:7][CH2:6]1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 133964-AminobenzonitrileHCID 199689354-chloro-6,7-dihydro-5H-cyclopenta[d]pyrimidin-7-yl acetate

Product 1

HCID 139132267-Acetoxy-4-(4-cyanoanilino)-6,7-dihydro-5H-cyclopenta[d]pyrimidineYield 55.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

39.3 g of 7-acetoxy-4-chloro-6,7-dihydro-5H-cyclopenta[d]pyrimidine [prepared as described in step (b) above] and 24 g of p-aminobenzonitrile were dissolved in 180 ml of ethanol, and the solution was heated under reflux for 1.5 hours. At the end of this time, the solvent was evaporated off under reduced pressure, and the resulting residue was washed with a 1:1 by volume mixture of ethanol and toluene, to give 30 g of the title compound as pale grayish crystals, melting at 215°-217° C.

Workup

  1. temperaturethe solution was heated
  2. temperatureunder reflux for 1.5 hours
  3. customAt the end of this time, the solvent was evaporated off under reduced pressure
  4. washthe resulting residue was washed with a 1:1 by volume mixture of ethanol and toluene

Sources & evidence

ORD record
ord-064491002d1040118ff9c94364c8cb47
Source dataset
uspto-grants-1988_06
Patent number
US04749704

Reaction notes

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