HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

Cyclohexylisopropylamine → 3-(2,4-Dichloro-pyrimidin-5-yl)-2-pyridin-4-yl-propionic acid ethyl ester

HRID 11784
Notes
Print preview

Reaction equation

HRID 11784 reaction equation
C(NC1CCCCC1)(C)C.C([Li])CCC.[CH2:16]([O:18][C:19](=[O:27])[CH2:20][C:21]1[CH:26]=[CH:25][N:24]=[CH:23][CH:22]=1)[CH3:17].[Cl:28][C:29]1[N:34]=[C:33]([Cl:35])[C:32]([CH2:36]I)=[CH:31][N:30]=1>O1CCCC1.C(OCC)(=O)C>[CH2:16]([O:18][C:19](=[O:27])[CH:20]([C:21]1[CH:26]=[CH:25][N:24]=[CH:23][CH:22]=1)[CH2:36][C:32]1[C:33]([Cl:35])=[N:34][C:29]([Cl:28])=[N:30][CH:31]=1)[CH3:17]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 62386CyclohexylisopropylamineHCID 736321Ethyl pyridine-4-acetateHCID 219393522,4-Dichloro-5-(iodomethyl)pyrimidineHCID 178418339Butyllithium

Product 1

HCID 210443043-(2,4-Dichloro-pyrimidin-5-yl)-2-pyridin-4-yl-propionic acid ethyl ester

Reagents, catalysts & solvents 2

HCID 8028
Tetrahydrofuran
Solvent
3×
HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of N-isopropylcyclohexylamine (720 mg, 5.0 mmol) (Aldrich) in dry tetrahydrofuran (10 mL) was added n-butyllithium (2.5 M in hexanes, 2.0 mL, 5.0 mmol) (Aldrich) at −78° C. under argon. After 30 minutes, a solution of 4-pyridylacetic acid ethyl ester (826 mg, 5.0 mmol) (Lancaster) in tetrahydrofuran (3 mL) was added by injection via a syringe and the reaction mixture was stirred at −78° C. for another 30 minutes. To the reaction mixture was added a solution of 2,4-dichloro-5-iodomethyl-pyrimidine (722.5 mg, 2.5 mmol) (from Example 1c supra) in tetrahydrofuran (3 mL) at −78° C. and the reaction mixture was stirred at the same temperature for 1 hour then slowly allowed to warm up to −30° C. and stirred for 10 minutes. The reaction mixture was diluted with ethyl acetate (100 mL) and successively washed with saturated aqueous ammonium chloride solution (50 mL), water (30 mL) and brine (30 mL), dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo to give the crude 3-(2,4-dichloro-pyrimidin-5-yl)-2-pyridin-4-yl-propionic acid ethyl ester which was used in the next step without further purification. (Yield 1.43 g, 83.6%).

Workup

  1. stirringthe reaction mixture was stirred at the same temperature for 1 hour
  2. temperatureto warm up to −30° C.
  3. stirringstirred for 10 minutes
  4. washsuccessively washed with saturated aqueous ammonium chloride solution (50 mL), water (30 mL) and brine (30 mL)
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-014700ab78b24173b0516adc76ae8891
Source dataset
uspto-grants-2006_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07098332B2

Reaction notes

Loading…

On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes