Cycloheptylamine → 6-chloro-N2-(3-chloro-4-methoxy-phenyl)-N4-cycloheptyl-pyrimidine-2,4-diamine

HRID 1161655Notes

Reaction equation

HRID 1161655 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:10][C:11]2[N:16]=[C:15](Cl)[CH:14]=[C:13]([Cl:18])[N:12]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].[CH:19]1([NH2:26])[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1.C(N(CC)CC)C>C(O)CCC>[Cl:18][C:13]1[N:12]=[C:11]([NH:10][C:4]2[CH:5]=[CH:6][C:7]([O:8][CH3:9])=[C:2]([Cl:1])[CH:3]=2)[N:16]=[C:15]([NH:26][CH:19]2[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]2)[CH:14]=1

Participants

5

Reactant 3

HCID 2899CycloheptylamineHCID 8471TriethylamineHCID 58626087(3-Chloro-4-methoxy-phenyl)-(4,6-dichloro-pyrimidin-2-yl)-amine

Product 1

HCID 586260766-chloro-N2-(3-chloro-4-methoxy-phenyl)-N4-cycloheptyl-pyrimidine-2,4-diamineYield 60%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

To a solution of compound (3-chloro-4-methoxy-phenyl)-(4,6-dichloro-pyrimidin-2-yl)-amine (0.08 g, 0.26 mmol) in butanol (3 mL) was added to cycloheptylamine (0.03 g, 0.26 mmol) at 25° C. with stirring. To this was added triethylamine (0.14 mL, 1.04 mmol), and the mixture was stirred for 30 minutes at 25° C. and then heated and refluxed for 12 hours under nitrogen atmosphere. The mixture was concentrated under vacuum, diluted with cold water, and extracted with ethyl acetate. The organic layers were collected, combined, washed with brine, dried over anhydrous sodium sulphate, and concentrated under vacuum to give the desired compound. Yield: 60%.

Workup

  1. stirringthe mixture was stirred for 30 minutes at 25° C.
  2. temperatureheated
  3. temperaturerefluxed for 12 hours under nitrogen atmosphere
  4. concentrationThe mixture was concentrated under vacuum
  5. additiondiluted with cold water
  6. extractionextracted with ethyl acetate
  7. customThe organic layers were collected
  8. washwashed with brine
  9. dry with materialdried over anhydrous sodium sulphate
  10. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-6e5260e4ff7e44e7abdb032391bb80f7
Source dataset
uspto-grants-2010_10
Patent number
US07820654B2

Reaction notes

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