Ethyl Acetate → HCID 86626749, compound

HRID 603988Notes

Reaction equation

HRID 603988 reaction equation
[F:1][C:2]([F:34])([F:33])[C:3]1[CH:4]=[C:5]([CH:26]=[C:27]([C:29]([F:32])([F:31])[F:30])[CH:28]=1)[CH2:6][NH:7][CH2:8][C:9]1[CH:14]=[C:13]([C:15]([F:18])([F:17])[F:16])[CH:12]=[CH:11][C:10]=1[N:19]([CH2:24][CH3:25])[CH2:20][CH2:21][O:22][CH3:23].[Br:35][C:36]1[CH:37]=[N:38][C:39](Cl)=[N:40][CH:41]=1.C(N(C(C)C)C(C)C)C.C(OCC)(=O)C>C1(C)C=CC=CC=1.O>[F:1][C:2]([F:33])([F:34])[C:3]1[CH:4]=[C:5]([CH:26]=[C:27]([C:29]([F:32])([F:30])[F:31])[CH:28]=1)[CH2:6][N:7]([C:39]1[N:40]=[CH:41][C:36]([Br:35])=[CH:37][N:38]=1)[CH2:8][C:9]1[CH:14]=[C:13]([C:15]([F:18])([F:16])[F:17])[CH:12]=[CH:11][C:10]=1[N:19]([CH2:24][CH3:25])[CH2:20][CH2:21][O:22][CH3:23]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 81531DiisopropylethylamineHCID 6066655-Bromo-2-chloropyrimidineHCID 86626748HCID 86626748, compound

Product 1

HCID 86626749HCID 86626749, compoundYield 91.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
120 °C

Procedure

{2-[(3,5-Bis-trifluoromethyl-benzylamino)-methyl]-4-trifluoromethyl-phenyl}-ethyl-(2-methoxy-ethyl)-amine (3.37 g), 5-bromo-2-chloropyrimidine (2.6 g) and N-ethyldiisopropylamine (3.51 ml) are dissolved in toluene (50 ml) and the mixture is stirred at 120° C. overnight. The reaction solution is cooled to room temperature, and thereto are added ethyl acetate and water and the mixture is separated, and the organic layer is washed with a saturated brine, and the mixture is dried over magnesium sulfate and is concentrated under reduced pressure. The resulting residue is purified by silica gel column chromatography (hexane:ethyl acetate=1:0→19:1) to give (3,5-bis-trifluoromethyl-benzyl)-(5-bromopyrimidin-2-yl)-{2-[ethyl-(2-methoxy-ethyl)-amino]-5-trifluoromethyl-benzyl}-amine (4.06 g). MS (m/z): 659/661 [M+H]+

Workup

  1. temperatureThe reaction solution is cooled to room temperature
  2. customthe mixture is separated
  3. washthe organic layer is washed with a saturated brine
  4. dry with materialthe mixture is dried over magnesium sulfate
  5. concentrationis concentrated under reduced pressure
  6. customThe resulting residue is purified by silica gel column chromatography (hexane:ethyl acetate=1:0→19:1)

Sources & evidence

ORD record
ord-fa27bff013d64d30b53af4a888c379d9
Source dataset
uspto-grants-2011_03
Patent number
US07906517B2

Reaction notes

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