Water → Ethyl 4-(5-bromopyrimidin-2-ylamino)-1-methylcyclohexanecarboxylate

HRID 712247Notes

Reaction equation

HRID 712247 reaction equation
[NH2:1][CH:2]1[CH2:7][CH2:6][C:5]([CH3:13])([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:4][CH2:3]1.CCN(C(C)C)C(C)C.[Br:23][C:24]1[CH:25]=[N:26][C:27](Cl)=[N:28][CH:29]=1.O>CCO>[Br:23][C:24]1[CH:25]=[N:26][C:27]([NH:1][CH:2]2[CH2:3][CH2:4][C:5]([CH3:13])([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:6][CH2:7]2)=[N:28][CH:29]=1

Participants

6

Reactant 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 6066655-Bromo-2-chloropyrimidineHCID 58291914Ethyl 4-amino-1-methylcyclohexanecarboxylate

Product 1

HCID 66976994Ethyl 4-(5-bromopyrimidin-2-ylamino)-1-methylcyclohexanecarboxylateYield 19.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

To an ice-cold solution of ethyl 4-amino-1-methylcyclohexanecarboxylate (0.18 g, 0.97 mmol) in EtOH (5.0 mL) was added DIPEA (0.52 mL, 2.91 mmol) followed by the addition of 5-bromo-2-chloropyrimidine (0.185 g, 0.97 mmol). The mixture was heated to 80° C. for 6-8 h after then cooled to rt, water added and extracted with EtOAc (3×100 mL). The combined organics were washed with brine, dried over anhydrous Na2SO4, filtered and evaporated under reduced pressure. The crude residue was purified over 100-200 M silica-gel by using 4% EtOAc:hexane to obtain the desired product (0.064 g, 19%). MS: 342.01 [M+H]+.

Workup

  1. temperatureafter then cooled to rt
  2. extractionextracted with EtOAc (3×100 mL)
  3. washThe combined organics were washed with brine
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. customevaporated under reduced pressure
  7. customThe crude residue was purified over 100-200 M silica-gel

Sources & evidence

ORD record
ord-242d835b2ee14af2b83f77d8d840a3d5
Source dataset
uspto-grants-2015_11
Patent number
US09181234B2

Reaction notes

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