Potassium Carbonate → HCID 178517732, compound

HRID 705801Notes

Reaction equation

HRID 705801 reaction equation
Cl.[Br:2][C:3]1[CH:4]=[C:5]([CH2:10][CH2:11][C:12](=[NH:14])[NH2:13])[CH:6]=[CH:7][C:8]=1[F:9].C(=O)([O-])[O-].[K+].[K+].[CH:21]([CH:23]([CH2:29][C:30]1[CH:31]=[N:32][CH:33]=[N:34][CH:35]=1)[C:24](OCC)=O)=[O:22]>C1(C)C=CC=CC=1.O>[Br:2][C:3]1[CH:4]=[C:5]([CH:6]=[CH:7][C:8]=1[F:9])[CH2:10][CH2:11][C:12]1[NH:13][CH:24]=[C:23]([CH2:29][C:30]2[CH:35]=[N:34][CH:33]=[N:32][CH:31]=2)[C:21](=[O:22])[N:14]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 21936283Ethyl 2-formyl-3-(5-pyrimidyl)propionateHCID 677757593-(3-Bromo-4-fluorophenyl)propanimidamide hydrochloride

Product 1

HCID 178517732HCID 178517732, compoundYield 79.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
115 °C

Procedure

The mixture of 3-(3-bromo-4-fluorophenyl)propanimidamide hydrochloride (5.0 g, 19.38 mmol), potassium carbonate (9.37 g, 67.8 mmol) and ethyl 2-formyl-3-(5-pyrimidinyl)propanoate (4.03 g, 20.35 mmol) in toluene (100 mL) was stirred at 115° C. for 2.5 h. After cooling, the mixture was diluted with water, then extracted with DCM (50 mL×2). The combined organic phase was concentrated to give the crude title compound as a light yellow solid (6.0 g, 77% yield). The crude was used without further purification. LCMS: rt=1.20 min, [M+H+]=389

Workup

  1. temperatureAfter cooling
  2. extractionextracted with DCM (50 mL×2)
  3. concentrationThe combined organic phase was concentrated

Sources & evidence

ORD record
ord-43b510d7245d458dbfd962cea4f2fbc8
Source dataset
uspto-grants-2015_11
Patent number
US09174968B2

Reaction notes

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