2-Aminopyrimidine → (+/-)-2-[3,5-dichloro-4-[(4-chlorophenyl)[(2-pyrimidinyl)amino]-methyl]phenyl]-1,2,4-triazine-3,5 (2H,4H)-dione

HRID 984049Notes

Reaction equation

HRID 984049 reaction equation
Cl[CH:2]([C:19]1[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=1)[C:3]1[C:8]([Cl:9])=[CH:7][C:6]([N:10]2[C:15](=[O:16])[NH:14][C:13](=[O:17])[CH:12]=[N:11]2)=[CH:5][C:4]=1[Cl:18].[N:26]1[CH:31]=[CH:30][CH:29]=[N:28][C:27]=1[NH2:32]>C(Cl)Cl>[Cl:18][C:4]1[CH:5]=[C:6]([N:10]2[C:15](=[O:16])[NH:14][C:13](=[O:17])[CH:12]=[N:11]2)[CH:7]=[C:8]([Cl:9])[C:3]=1[CH:2]([C:19]1[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=1)[NH:32][C:27]1[N:28]=[CH:29][CH:30]=[CH:31][N:26]=1

Participants

4

Reactant 2

HCID 79782-AminopyrimidineHCID 22557370HCID 22557370, compound

Product 1

HCID 22557399(+/-)-2-[3,5-dichloro-4-[(4-chlorophenyl)[(2-pyrimidinyl)amino]-methyl]phenyl]-1,2,4-triazine-3,5 (2H,4H)-dioneYield 6.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 2-[4-[chloro(4-chlorophenyl)methyl]-3,5-dichlorophenyl]-1,2,4-triazine-3,5(2H,4H)-dione (0.00719 mol) and 2-pyrimidinamine (0.00863 mol) was heated for 2 hours at 150° C. in an autoclave. The mixture was cooled to RT. This fraction was taken up into CH2Cl2, washed with water, dried, filtered and the solvent was evaporated. The residue was purified by HPLC (eluent: (0.5% NH4OAc in H2O)/CH3OH/CH3CN gradient elution from 70/15/15 over 0/50/50 to 0/0/100). The desired fractions were collected and the solvent was evaporated. The residue was coevaporated with EtOAc. The residue was stirred in DIPE, filtered off, washed and dried, yielding 0.21 g of (±)-2-[3,5-dichloro-4-[(4-chlorophenyl)[(2-pyrimidinyl)amino]-methyl]phenyl]-1,2,4-triazine-3,5(2H,4H)-dione (comp. 413).

Workup

  1. temperatureThe mixture was cooled to RT
  2. washwashed with water
  3. customdried
  4. filtrationfiltered
  5. customthe solvent was evaporated
  6. customThe residue was purified by HPLC (eluent: (0.5% NH4OAc in H2O)/CH3OH/CH3CN gradient elution from 70/15/15 over 0/50/50 to 0/0/100)
  7. customThe desired fractions were collected
  8. customthe solvent was evaporated
  9. filtrationfiltered off
  10. washwashed
  11. customdried

Sources & evidence

ORD record
ord-d9696c786db9411e9e999afd3a9e0a04
Source dataset
uspto-grants-2005_03
Patent number
US06867207B2

Reaction notes

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