Cyclohexylamine → HCID 53259301, compound

HRID 876177Notes

Reaction equation

HRID 876177 reaction equation
Cl[C:2]1[CH:7]=[C:6](Cl)[N:5]=[CH:4][N:3]=1.[CH3:9][O:10][C:11]1[CH:12]=[C:13]([CH:15]=[CH:16][CH:17]=1)[NH2:14].CCN(C(C)C)C(C)C.[CH:27]1([NH2:33])[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]1>CCCCO>[CH:27]1([NH:33][C:2]2[CH:7]=[C:6]([NH:14][C:13]3[CH:15]=[CH:16][CH:17]=[C:11]([O:10][CH3:9])[CH:12]=3)[N:5]=[CH:4][N:3]=2)[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]1

Participants

6

Reactant 4

HCID 7965CyclohexylamineHCID 108243-MethoxyanilineHCID 709434,6-DichloropyrimidineHCID 81531Diisopropylethylamine2×

Product 1

HCID 53259301HCID 53259301, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

100 mg of 4,6-dichloropyrimidine, 83 mg of 3-methoxyaniline and 103 mg of DIPEA were dissolved in 1 mL of n-BuOH and the mixture obtained was charged into a microwave vial and the vial obtained was kept in a heating block at 120° C. for 6 hours. The reaction was monitored by TLC and was completed after 6 hours. The mixture obtained was cooled to r.t., 100 mg of cyclohexylamine and 139 mg of DIPEA were added and the mixture obtained was heated under microwave irradiation for an hour at 200° C. The reaction was finished and pure product was purified by column chromatography using PE:EtOAc 2:1. Pure N4-Cyclohexyl-N6-(3-methoxyphenyl)pyrimidine-4,6-diamine in the form of a colorless solid was obtained.

Workup

  1. customthe mixture obtained
  2. additionwas charged into a microwave vial
  3. customthe vial obtained
  4. waitwas completed after 6 hours
  5. customThe mixture obtained
  6. customthe mixture obtained
  7. temperaturewas heated under microwave irradiation for an hour at 200° C
  8. custompure product was purified by column chromatography

Sources & evidence

ORD record
ord-5facff9994b1476b82e862b4395d9f0a
Source dataset
uspto-grants-2015_03
Patent number
US08986994B2

Reaction notes

Loading…