Pyrrolidine → HCID 19428500, compound

HRID 1721293Notes

Reaction equation

HRID 1721293 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6](Cl)[N:5]=[C:4]([NH:9][C:10]23[CH2:19][CH:14]4[CH2:15][CH:16]([CH2:18][CH:12]([CH2:13]4)[CH2:11]2)[CH2:17]3)[N:3]=1.[NH:20]1[CH2:24][CH2:23][CH2:22][CH2:21]1>>[C:10]12([NH:9][C:4]3[N:3]=[C:2]([Cl:1])[CH:7]=[C:6]([N:20]4[CH2:24][CH2:23][CH2:22][CH2:21]4)[N:5]=3)[CH2:11][CH:12]3[CH2:13][CH:14]([CH2:15][CH:16]([CH2:18]3)[CH2:17]1)[CH2:19]2

Participants

3

Reactant 2

HCID 31268PyrrolidineHCID 19428536HCID 19428536, compound

Product 1

HCID 19428500HCID 19428500, compound

Procedure

10 g (33.53 mmoles) of 4,6-dichloro-2-(1-adamantylamino)pyrimidine are added in small portions to 40 ml of pyrrolidine at a temperature below 10° C. under cooling and stirring. After addition the reaction mixture is stirred at room temperature for 1 hour, then evaporated. The residue is distributed between 150 ml of chloroform and 30 ml of 10% sodium hydroxide solution. After separation the organic phase is washed 4 times with 50 ml of water each, then dried and evaporated. The evaporation residue is recrystallized from ethyl acetate to give the title compound in a yield of 9.60 g (86%), m.p.: 178°-180° C.

Workup

  1. temperatureunder cooling
  2. additionAfter addition the reaction mixture
  3. stirringis stirred at room temperature for 1 hour
  4. customevaporated
  5. customAfter separation the organic phase
  6. washis washed 4 times with 50 ml of water each,
  7. customthen dried
  8. customevaporated
  9. customThe evaporation residue is recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-d518352b55b049d3af45f1c61a0335c9
Source dataset
uspto-grants-1996_04
Patent number
US05510345

Reaction notes

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