2,4-Dichloropyrimidine → (S)-2-(2-chloropyrimidin-4-ylamino)-N-(2,2,2-trifluoroethyl)propanamide

HRID 1409114Notes

Reaction equation

HRID 1409114 reaction equation
[NH2:1][C@@H:2]([CH3:11])[C:3]([NH:5][CH2:6][C:7]([F:10])([F:9])[F:8])=[O:4].[Cl:12][C:13]1[N:18]=[C:17](Cl)[CH:16]=[CH:15][N:14]=1>C(O)(C)C.C(OCC)(=O)C>[Cl:12][C:13]1[N:18]=[C:17]([NH:1][C@@H:2]([CH3:11])[C:3]([NH:5][CH2:6][C:7]([F:8])([F:9])[F:10])=[O:4])[CH:16]=[CH:15][N:14]=1

Participants

5

Reactant 2

HCID 775312,4-DichloropyrimidineHCID 28172283(S)-2-amino-N-(2,2,2-trifluoroethyl)propanamide

Product 1

HCID 58897098(S)-2-(2-chloropyrimidin-4-ylamino)-N-(2,2,2-trifluoroethyl)propanamide

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (S)-2-amino-N-(2,2,2-trifluoroethyl)propanamide (FF) (1 g, 3.35 mol, 1 equiv.) in iso-propanol (10 mL), Huning's base (1.5 mL) was added, followed by 2,4-dichloropyrimidine (JJ). The resulting mixture was refluxed for 18 h. The reaction mixture was then diluted in ethyl acetate, washed with aqueous HCl 0.5 M and water, and dried over anhydrous Na2SO4. The crude oil was then purified by flash chromatography on silica gel, eluting with hexanes/ethyl acetate mixtures (100:0 to 0:100). The title compound HH was isolated as a white solid (600 mg, 63%).

Workup

  1. temperatureThe resulting mixture was refluxed for 18 h
  2. washwashed with aqueous HCl 0.5 M and water
  3. dry with materialdried over anhydrous Na2SO4
  4. customThe crude oil was then purified by flash chromatography on silica gel
  5. washeluting with hexanes/ethyl acetate mixtures (100:0 to 0:100)

Sources & evidence

ORD record
ord-07dba9537ba245b3b2cf87cda0faf57d
Source dataset
uspto-grants-2014_12
Patent number
US08921376B2

Reaction notes

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