Trifluoroacetic acid → (R)-1-(2-fluoro-6-(trifluoromethyl)benzyl)-3-(2-amino-2-phenylethyl)-5-(2-chloro-3-methoxyphenyl)pyrimidine-2,4(1H,3H)-dione

HRID 1790078Notes

Reaction equation

HRID 1790078 reaction equation
C(OC([NH:8][C@H:9]([C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)[CH2:10][N:11]1[C:16](=[O:17])[C:15]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([O:24][CH3:25])[C:19]=2[Cl:26])=[CH:14][N:13]([CH2:27][C:28]2[C:33]([C:34]([F:37])([F:36])[F:35])=[CH:32][CH:31]=[CH:30][C:29]=2[F:38])[C:12]1=[O:39])=O)(C)(C)C.C(O)(C(F)(F)F)=O>ClCCl>[NH2:8][C@H:9]([C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)[CH2:10][N:11]1[C:16](=[O:17])[C:15]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([O:24][CH3:25])[C:19]=2[Cl:26])=[CH:14][N:13]([CH2:27][C:28]2[C:33]([C:34]([F:36])([F:35])[F:37])=[CH:32][CH:31]=[CH:30][C:29]=2[F:38])[C:12]1=[O:39]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 210837243-[2(R)-(tert-butoxycarbonylamino)-2-phenylethyl]-5-(2-chloro-3-methoxyphenyl)-1-[2-fluoro-6-(trifluoromethyl)benzyl]pyrimidine-2,4(1H,3H)-dione

Product 1

HCID 11376252(R)-1-(2-fluoro-6-(trifluoromethyl)benzyl)-3-(2-amino-2-phenylethyl)-5-(2-chloro-3-methoxyphenyl)pyrimidine-2,4(1H,3H)-dioneYield 96%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Compound 3g (2.7 g, 4.2 mmol) was dissolved in dichloromethane (10 mL), TFA (14 mL, 175 mmol) was added, and the mixture was stirred at room temperature for 4.5 hours. After concentration, the residue was taken up in DCM and saturated aq. NaHCO3 was added. The aq. layer was extracted with DCM. Combined organic extracts were dried over Na2SO4 and concentrated to give compound 3h (2.2 g, 96%). MS (CI) m/z 548.0, 550.0 (MH+).

Workup

  1. concentrationAfter concentration
  2. additionsaturated aq. NaHCO3 was added
  3. extractionThe aq. layer was extracted with DCM
  4. dry with materialCombined organic extracts were dried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-db3ac4cd835c4a7ba8019567c9b9395c
Source dataset
uspto-grants-2006_07
Patent number
US07071200B2

Reaction notes

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