Potassium Carbonate → (5-Methyl-2-trifluoromethyl-phenyl)-[(R)-3-(2-phenyl-pyrimidin-4-ylamino)-pyrrolidin-1-yl]-methanone

HRID 598517Notes

Reaction equation

HRID 598517 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:3]=1.[NH2:14][C@@H:15]1[CH2:19][CH2:18][N:17]([C:20]([C:22]2[CH:27]=[C:26]([CH3:28])[CH:25]=[CH:24][C:23]=2[C:29]([F:32])([F:31])[F:30])=[O:21])[CH2:16]1.C([O-])([O-])=O.[K+].[K+]>CN(C)C(=O)C>[CH3:28][C:26]1[CH:25]=[CH:24][C:23]([C:29]([F:32])([F:30])[F:31])=[C:22]([C:20]([N:17]2[CH2:18][CH2:19][C@@H:15]([NH:14][C:2]3[CH:7]=[CH:6][N:5]=[C:4]([C:8]4[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=4)[N:3]=3)[CH2:16]2)=[O:21])[CH:27]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 2591574-Chloro-2-phenylpyrimidineHCID 57748952((R)-3-Amino-pyrrolidin-1-yl)-(5-methyl-2-trifluoromethyl-phenyl)-methanone2×

Product 1

HCID 57748972(5-Methyl-2-trifluoromethyl-phenyl)-[(R)-3-(2-phenyl-pyrimidin-4-ylamino)-pyrrolidin-1-yl]-methanoneYield 46%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

A solution of 30 mg (0.16 mmol) 4-chloro-2-phenyl-pyrimidine (CAS: 14790-42-2), 42.8 mg (0.16 mmol) ((R)-3-Amino-pyrrolidin-1-yl)-(5-methyl-2-trifluoromethyl-phenyl)-methanone (intermediate 13), 54.3 mg (0.39 mmol) K2CO3 and 6.5 mg (0.039 mmol) KI in 1 mL N,N-dimethylacetamide was heated in a 60° C. for 2 h, and at 100° C. for 23 h. The solvent was removed in vacuo. The residue was dissolved in ethyl acetate and washed twice with water. The organic layer was dried with Na2SO4 and filtered. The mixture was concentrated and purified with flash column chromatography on silica eluting with a gradient formed from n-heptane and ethyl acetate to provide 31 mg (46%) of the titled compound as a light yellow solid. MS(m/e): 427.2 (M+H+).

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionThe residue was dissolved in ethyl acetate
  3. washwashed twice with water
  4. dry with materialThe organic layer was dried with Na2SO4
  5. filtrationfiltered
  6. concentrationThe mixture was concentrated
  7. custompurified with flash column chromatography on silica eluting with a gradient
  8. customformed from n-heptane and ethyl acetate

Sources & evidence

ORD record
ord-99bd195fce91450b8b628297eccd0939
Source dataset
uspto-grants-2011_03
Patent number
US07897627B2

Reaction notes

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