Chloroform → 5-Bromo-2-{2-[2-(4-trifluoromethyl-phenyl)-vinyl]-oxazol-4-ylmethoxy}-pyrimidine

HRID 349223Notes

Reaction equation

HRID 349223 reaction equation
[OH:1][CH2:2][C:3]1[N:4]=[C:5]([CH:8]=[CH:9][C:10]2[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][CH:11]=2)[O:6][CH:7]=1.CC([O-])(C)C.[Na+].[Br:26][C:27]1[CH:28]=[N:29][C:30](Cl)=[N:31][CH:32]=1.C(Cl)(Cl)Cl>O1CCCC1>[Br:26][C:27]1[CH:28]=[N:29][C:30]([O:1][CH2:2][C:3]2[N:4]=[C:5]([CH:8]=[CH:9][C:10]3[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][CH:11]=3)[O:6][CH:7]=2)=[N:31][CH:32]=1

Participants

6

Reactant 4

HCID 6212ChloroformHCID 6066655-Bromo-2-chloropyrimidineHCID 23676156Sodium t-butoxideHCID 68502458(2-{2-[4-(Trifluoromethyl)phenyl]ethenyl}-1,3-oxazol-4-yl)methanol

Product 1

HCID 694890165-Bromo-2-{2-[2-(4-trifluoromethyl-phenyl)-vinyl]-oxazol-4-ylmethoxy}-pyrimidineYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

4-Hydroxymethyl-2-[2-(4-trifluoromethyl-phenyl)-vinyl]-oxazole (0.538 g, 2.0 mmol) is dissolved in anhydrous tetrahydrofuran (THF) (10 ml) followed by the addition of NaOtBu (0.231 g, 2.4 mmol). After stirring for 15 min at r.t., 5-bromo-2-chloro-pyrimidine (0.426 g, 2.2 mmol) in THF (5 ml) is added slowly over a period of 10 min and stirred for further 30 min at r.t. Chloroform (25 ml) is added; the mixture is washed with 0.5N hydrochloric acid (HCl) and water, dried over MgSO4 and concentrated in vacuo. After flash column chromatography (100% chloroform) 5-bromo-2-{2-[2-(4-trifluoromethyl-phenyl)-vinyl]-oxazol-4-yl-methoxy}-pyrimidine can be isolated as an off-white solid. Yield 0.60 g (71%).

Workup

  1. stirringstirred for further 30 min at r.t
  2. washthe mixture is washed with 0.5N hydrochloric acid (HCl) and water
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5c4a0f186777492ca0b5df6c6bfffcd1
Source dataset
uspto-grants-2007_02
Patent number
US07179812B2

Reaction notes

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