Ethyl Acetate → 5-(4-[1,2,3]Triazol-1-yl-butyl)-2-{2-[2-(4-trifluoromethoxy-phenyl)-vinyl]-oxazol-4-ylmethoxy}-pyrimidine

HRID 349234Notes

Reaction equation

HRID 349234 reaction equation
[F:1][C:2]([F:20])([F:19])[O:3][C:4]1[CH:9]=[CH:8][C:7]([CH:10]=[CH:11][C:12]2[O:13][CH:14]=[C:15]([CH2:17][OH:18])[N:16]=2)=[CH:6][CH:5]=1.CC(C)([O-])C.[Na+].Cl[C:28]1[N:33]=[CH:32][C:31]([CH2:34][CH2:35][CH2:36][CH2:37][N:38]2[CH:42]=[CH:41][N:40]=[N:39]2)=[CH:30][N:29]=1.C(OCC)(=O)C>O1CCCC1>[N:38]1([CH2:37][CH2:36][CH2:35][CH2:34][C:31]2[CH:32]=[N:33][C:28]([O:18][CH2:17][C:15]3[N:16]=[C:12]([CH:11]=[CH:10][C:7]4[CH:8]=[CH:9][C:4]([O:3][C:2]([F:1])([F:19])[F:20])=[CH:5][CH:6]=4)[O:13][CH:14]=3)=[N:29][CH:30]=2)[CH:42]=[CH:41][N:40]=[N:39]1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 23676156Sodium t-butoxideHCID 68934459{2-[2-(4-Trifluoromethoxy-phenyl)-vinyl]-oxazol-4-yl}-methanolHCID 860740662-Chloro-5-(4-[1,2,3]triazol-1-yl-butyl)-pyrimidine

Product 1

HCID 691357885-(4-[1,2,3]Triazol-1-yl-butyl)-2-{2-[2-(4-trifluoromethoxy-phenyl)-vinyl]-oxazol-4-ylmethoxy}-pyrimidine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

{2-[2-(4-Trifluoromethoxy-phenyl)-vinyl]-oxazol-4-yl}-methanol (0.097 g, 0.34 mmol) is dissolved in anhydrous tetrahydrofuran (THF) (4 ml) followed by addition of sodium tert-butoxide (NaOtBu) (0.040 g, 0.41 mmol). After stirring for 15 min at r.t. 2-chloro-5-(4-[1,2,3]triazol-1-yl-butyl)-pyrimidine (0.090 g, 0.38 mmol) is added slowly and stirred for further 1.5 h at r.t. Ethyl acetate (20 ml) is added; the mixture is washed with saturated ammonium chloride (NH4Cl), dried over MgSO4 and concentrated in vacuo. After flash column chromatography (ethyl acetate) 5-(4-[1,2,3]triazol-1-yl-butyl)-2-{2-[2-(4-trifluoromethoxy-phenyl)-vinyl]-oxazol-4-ylmethoxy}-pyrimidine is obtained as a colorless solid. Yield 0.104 g (63%).

Workup

  1. stirringstirred for further 1.5 h at r.t
  2. washthe mixture is washed with saturated ammonium chloride (NH4Cl)
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-54d7261538974307915f91f2c6e820cc
Source dataset
uspto-grants-2007_02
Patent number
US07179812B2

Reaction notes

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