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

HRID 1790079Notes

Reaction equation

HRID 1790079 reaction equation
C(OC([NH:8][C@H:9]([CH2:40][CH:41]([CH3:43])[CH3:42])[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>C(Cl)Cl>[NH2:8][C@H:9]([CH2:40][CH:41]([CH3:43])[CH3:42])[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 210276743-[2(R)-{tert-butoxycarbonyl-amino}-2-(isobutyl)ethyl]-5-(2-chloro-3-methoxyphenyl)-1-[2-fluoro-6-(trifluoromethyl)benzyl]pyrimidine-2,4(1H,3H)-dione

Product 1

HCID 210276713-[2(R)-amino-2-(isobutyl)ethyl]-5-(2-chloro-3-methoxyphenyl)-1-[2-fluoro-6-(trifluoromethyl)benzyl]pyrimidine-2,4(1H,3H)-dione

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of compound 4a (30 mg, 0.048 mmol) in DCM (1 mL) was added TFA (0.1 mL, 1.3 mmol) and stirred at room temperature for 1.5 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 4b. MS (CI) m/z 528.0, 530.0 (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-e514aff2d8b1469695f26b9afac7cfd3
Source dataset
uspto-grants-2006_07
Patent number
US07071200B2

Reaction notes

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