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Sodium Chloride → 4-[(1R,2R)-2-benzyloxy-1-methyl-propoxy]-2-chloro-5-(trifluoromethyl)pyrimidine

HRID 1027848
Notes
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Reaction equation

HRID 1027848 reaction equation
[F-].[K+].[F:3][C:4]([Si](C)(C)C)([F:6])[F:5].[CH2:11]([O:18][C@H:19]([CH3:31])[C@@H:20]([CH3:30])[O:21][C:22]1[C:27](I)=[CH:26][N:25]=[C:24]([Cl:29])[N:23]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[Cl-].[Na+]>CN1C(=O)CCC1.C1COCC1.[Cu]I.CCCCCC.C(OCC)(=O)C>[CH2:11]([O:18][C@H:19]([CH3:31])[C@@H:20]([CH3:30])[O:21][C:22]1[C:27]([C:4]([F:6])([F:5])[F:3])=[CH:26][N:25]=[C:24]([Cl:29])[N:23]=1)[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

9

Reactant 4

HCID 5234Sodium ChlorideHCID 522689Potassium FluorideHCID 552549(Trifluoromethyl)trimethylsilaneHCID 584679604-((1R,2R)-2-benzyloxy-1-methylpropoxy)-2-chloro-5-iodopyrimidine

Product 1

HCID 468994684-[(1R,2R)-2-benzyloxy-1-methyl-propoxy]-2-chloro-5-(trifluoromethyl)pyrimidineYield 54%

Reagents, catalysts & solvents

4
HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 8028TetrahydrofuranSolventHCID 13387N-methyl-2-pyrrolidoneSolventHCID 21226206Ethyl acetate hexaneSolvent

Conditions

Temperature
80 °C

Procedure

3.82 g (20.0 mmol) of copper(I) iodide, 0.97 g (16.7 mmol) of potassium fluoride and 2.47 ml (16.7 mmol) (trifluoromethyl)-trimethylsilane were added, with stirring, to a solution of 4.66 g (11.1 mmol) of 4-((1R,2R)-2-benzyloxy-1-methyl-propoxy)-2-chloro-5-iodo-pyrimidine in 15.8 ml NMP and 15.8 ml THF at room temperature. The mixture was stirred for 5.5 hours at 80° C. After cooling, the mixture was added to dilute sodium chloride solution and was extracted with ethyl acetate (2×). The combined organic phases were dried (Na2SO4), filtered and concentrated by evaporation. The residue obtained was chromatographically (hexane/ethyl acetate 4:1). 2.17 g (6.0 mmol; yield: 54%) of the product was obtained.

Workup

  1. temperatureAfter cooling
  2. extractionwas extracted with ethyl acetate (2×)
  3. dry with materialThe combined organic phases were dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated by evaporation
  6. customThe residue obtained
  7. custom2.17 g (6.0 mmol; yield: 54%) of the product was obtained

Sources & evidence

ORD record
ord-b11f1ab87e774d5d816cced602bb59c8
Source dataset
uspto-grants-2014_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08735412B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes