Aniline → 4-Anilino-6,7-dihydro-5H-cyclopenta[d]pyrimidine hydrochloride

HRID 544383Notes

Reaction equation

HRID 544383 reaction equation
[Cl:1][C:2]1[C:3]2[CH2:10][CH2:9][CH2:8][C:4]=2[N:5]=[CH:6][N:7]=1.[NH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>C(O)C>[ClH:1].[NH:11]([C:2]1[C:3]2[CH2:10][CH2:9][CH2:8][C:4]=2[N:5]=[CH:6][N:7]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 6115AnilineHCID 133124494-chloro-5H,6H,7H-cyclopenta[d]pyrimidine

Product 1

HCID 204589374-Anilino-6,7-dihydro-5H-cyclopenta[d]pyrimidine hydrochlorideYield 59%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
100 °C

Procedure

To 3.1 g (0.02 mole) of 4-chloro-6,7-dihydro-5H-cyclopenta[d]pyrimidine were added 4.7 g (0.05 mole) of aniline and about 10 ml of ethanol; the mixture was then heated at 100° C. for about 10 minutes; the mixture quickly became a solution and then soon produced crystals. The mixture was then heated for a further 5 minutes, after which it was allowed to cool. The crystals produced were collected by filtration and then recrystallised from ethanol, to give 2.9 g (yield 59%) of the desiredCompound No. 2, in the form of yellow needles melting at 220° C. (with decomposition).

Workup

  1. temperatureThe mixture was then heated for a further 5 minutes
  2. temperatureto cool
  3. customThe crystals produced
  4. filtrationwere collected by filtration
  5. customrecrystallised from ethanol
  6. customto give 2.9 g (yield 59%) of the desiredCompound No

Sources & evidence

ORD record
ord-8b2b4214ce07495882ed798a29df820e
Source dataset
uspto-grants-1984_05
Patent number
US04450162

Reaction notes

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