Trifluoroacetic acid → 3-((R)-2-Amino-2-cyclohexyl-ethyl)-1-(2,6-difluoro-benzyl)-5-(2-fluoro-3-methoxy-phenyl)-6-methyl-1H-pyrimidine-2,4-dione

HRID 347778Notes

Reaction equation

HRID 347778 reaction equation
C(OC([NH:8][C@H:9]([CH:38]1[CH2:43][CH2:42][CH2:41][CH2:40][CH2:39]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[F:26])=[C:14]([CH3:27])[N:13]([CH2:28][C:29]2[C:34]([F:35])=[CH:33][CH:32]=[CH:31][C:30]=2[F:36])[C:12]1=[O:37])=O)(C)(C)C.C(O)(C(F)(F)F)=O>ClCCl>[NH2:8][C@H:9]([CH:38]1[CH2:43][CH2:42][CH2:41][CH2:40][CH2:39]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[F:26])=[C:14]([CH3:27])[N:13]([CH2:28][C:29]2[C:30]([F:36])=[CH:31][CH:32]=[CH:33][C:34]=2[F:35])[C:12]1=[O:37]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 589650063-[2(R)-tert-butoxycarbonylamino-2-cyclohexylethyl]-5-(2-fluoro-3-methoxyphenyl)-1-[2,6-difluorobenzyl]-6-methyl-pyrimidine-2,4(1H,3H)-dione

Product 1

HCID 111802193-((R)-2-Amino-2-cyclohexyl-ethyl)-1-(2,6-difluoro-benzyl)-5-(2-fluoro-3-methoxy-phenyl)-6-methyl-1H-pyrimidine-2,4-dione

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To compound 4c (300 mg, 0.5 mmol) in dichloromethane (2 mL) was added TFA (2 mL) and the reaction mixture was stirred at ambient temperature for 1 hour. Volatiles were evaporated and the residue was partitioned between saturated NaHCO3/water and EtOAc. The organic layer was dried (sodium sulfate), evaporated, purified by reverse phase HPLC (C-18 column, 15–75% ACN/water) to give compound 4d. MS (CI) m/z 502.2 (MH+).

Workup

  1. customVolatiles were evaporated
  2. customthe residue was partitioned between saturated NaHCO3/water and EtOAc
  3. dry with materialThe organic layer was dried (sodium sulfate)
  4. customevaporated
  5. custompurified by reverse phase HPLC (C-18 column, 15–75% ACN/water)

Sources & evidence

ORD record
ord-e826d36c283143cb95a6aab79eff985d
Source dataset
uspto-grants-2007_02
Patent number
US07176211B2

Reaction notes

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