Ethyl Acetate → HCID 67271115, compound

HRID 600855Notes

Reaction equation

HRID 600855 reaction equation
[C:1]([O:5][C:6]([N:8]1[C@@H:12]([CH2:13][NH:14][CH2:15][CH3:16])[CH2:11][O:10][C:9]1([CH3:18])[CH3:17])=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl[C:20]1[CH:25]=[CH:24][N:23]=[C:22]([C:26]([F:29])([F:28])[F:27])[N:21]=1.C(N(CC)C(C)C)(C)C.C(OCC)(=O)C>C(O)(C)C>[C:1]([O:5][C:6]([N:8]1[C@@H:12]([CH2:13][N:14]([CH2:15][CH3:16])[C:20]2[CH:25]=[CH:24][N:23]=[C:22]([C:26]([F:29])([F:28])[F:27])[N:21]=2)[CH2:11][O:10][C:9]1([CH3:17])[CH3:18])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 81531DiisopropylethylamineHCID 152943694-Chloro-2-(trifluoromethyl)pyrimidineHCID 67271691HCID 67271691, compound

Product 1

HCID 67271115HCID 67271115, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A solution of (S)-4-ethylaminomethyl-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (0.310 g, 1.2 mmol), 4-chloro-2-(trifluoromethyl)pyrimidine (0.183 g; 1.0 mmol) and N,N-diisopropyl ethyl amine (0.34 ml, 2.0 mmol) in isopropanol (3 ml) was heated in a sealed vessel in a microwave oven for 30 min at 180° C. Ethyl acetate (20 ml) and silicagel (1 g) was added and the mixture was evaporated. The residue was purified by flash chromatography, column: Isolute® Flash-NH2 (Separtis); eluent: EtOAc/MeOH=95:5) to yield a light yellow oil, (0.362 g, 90%); MS (ISP): 405.5 ((M+H)+).

Workup

  1. customthe mixture was evaporated
  2. customThe residue was purified by flash chromatography, column
  3. customeluent: EtOAc/MeOH=95:5) to yield a light yellow oil, (0.362 g, 90%)

Sources & evidence

ORD record
ord-f64833bbfff04e3784f71f9c86a97945
Source dataset
uspto-grants-2011_03
Patent number
US07902238B2

Reaction notes

Loading…