Cyclohexylamine → HCID 53259302, compound

HRID 876176Notes

Reaction equation

HRID 876176 reaction equation
Cl[C:2]1[CH:7]=[C:6](Cl)[N:5]=[CH:4][N:3]=1.[Cl:9][C:10]1[CH:11]=[C:12]([CH:14]=[CH:15][C:16]=1[O:17][CH3:18])[NH2:13].CCN(C(C)C)C(C)C.[CH:28]1([NH2:34])[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1>CCCCO>[Cl:9][C:10]1[CH:11]=[C:12]([NH:13][C:2]2[CH:7]=[C:6]([NH:34][CH:28]3[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]3)[N:5]=[CH:4][N:3]=2)[CH:14]=[CH:15][C:16]=1[O:17][CH3:18]

Participants

6

Reactant 4

HCID 7965CyclohexylamineHCID 214413-Chloro-4-methoxyanilineHCID 709434,6-DichloropyrimidineHCID 81531Diisopropylethylamine2×

Product 1

HCID 53259302HCID 53259302, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

100 mg of 4,6-dichloropyrimidine, 106 mg of 3-chloro-4-methoxyaniline and 103 mg of DIPEA were dissolved in 1 mL n-BuOH and the mixture obtained was charged into a microwave vial and kept overnight in a heating block at 120° C. The reaction was monitored by TLC and was completed after 12 hours. The mixture obtained was cooled to r.t., 100 mg of cyclohexylamine and 139 mg of DIPEA were added and mixture obtained was heated under microwave irradiation for an hour at 200° C. The reaction was finished and pure product was precipitated out from n-BuOH. The precipitate obtained was washed with cold n-BuOH. Pure N4-(3-chloro-4-methoxyphenyl)-N6-cyclohexylpyrimidine-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. waitwas completed after 12 hours
  4. customThe mixture obtained
  5. custommixture obtained
  6. temperaturewas heated under microwave irradiation for an hour at 200° C
  7. custompure product was precipitated out from n-BuOH
  8. customThe precipitate obtained
  9. washwas washed with cold n-BuOH

Sources & evidence

ORD record
ord-7c53f6946f0243a786fbc7062d13e445
Source dataset
uspto-grants-2015_03
Patent number
US08986994B2

Reaction notes

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