Amantadine Hydrochloride → 6-chloro-N-(1-Adamantyl)pyrimidin-4-amine

HRID 876156

Reaction equation

HRID 876156 reaction equation
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[CH:4][N:3]=1.Cl.[NH2:10][C:11]12[CH2:20][CH:15]3[CH2:16][CH:17]([CH2:19][CH:13]([CH2:14]3)[CH2:12]1)[CH2:18]2.CCN(C(C)C)C(C)C>CC(O)C>[C:11]12([NH:10][C:2]3[CH:7]=[C:6]([Cl:8])[N:5]=[CH:4][N:3]=3)[CH2:18][CH:17]3[CH2:16][CH:15]([CH2:14][CH:13]([CH2:19]3)[CH2:12]1)[CH2:20]2

Participants

5

Reactant 3

HCID 64150Amantadine HydrochlorideHCID 709434,6-DichloropyrimidineHCID 81531Diisopropylethylamine

Product 1

HCID 534860716-chloro-N-(1-Adamantyl)pyrimidin-4-amine

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

200 mg of 4,6-dichloropyrimidine, 252 mg of 1-aminoadamantane hydrochloride and 452 mg of DIPEA were dissolved in 2 mL of i-PrOH and the mixture obtained was charged into a screw cap vial and the vial was kept overnight in a heating block at 90° C. The reaction was monitored by TLC and was completed after 12 hours. The mixture obtained was cooled to r.t., solvent was evaporated and N-adamant-1-yl-6-chloropyrimidin-4-amine was obtained by column chromatography using PE:EtOAc 10:1.

Workup

  1. customthe mixture obtained
  2. additionwas charged into a screw
  3. customcap vial
  4. waitwas completed after 12 hours
  5. customThe mixture obtained
  6. customsolvent was evaporated

Sources & evidence

ORD record
ord-228abab036764f349acb295748861d3d
Source dataset
uspto-grants-2015_03
Patent number
US08986994B2

Linked notes

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