Sodium Hydroxide → HCID 23512560, compound

HRID 354018Notes

Reaction equation

HRID 354018 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:9]([NH:16][CH3:17])=[N:10][C:11]([S:14][CH3:15])=[N:12][CH:13]=1.C[Si](C)(C)[N-][Si](C)(C)C.[K+].[F:28][C:29]([F:47])([F:46])[C:30]1[CH:31]=[C:32]([C:40]([CH3:45])([CH3:44])[C:41](Cl)=[O:42])[CH:33]=[C:34]([C:36]([F:39])([F:38])[F:37])[CH:35]=1.[OH-].[Na+]>CN(C)C=O.C1COCC1.C(OCC)(=O)C>[F:39][C:36]([F:37])([F:38])[C:34]1[CH:33]=[C:32]([C:40]([CH3:45])([CH3:44])[C:41]([N:16]([C:9]2[C:8]([C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=3[Cl:1])=[CH:13][N:12]=[C:11]([S:14][CH3:15])[N:10]=2)[CH3:17])=[O:42])[CH:31]=[C:30]([C:29]([F:46])([F:28])[F:47])[CH:35]=1

Participants

8

Reactant 4

HCID 14798Sodium HydroxideHCID 3251421Potassium bis(trimethylsilyl)amideHCID 112671412-(3,5-Bis(trifluoromethyl)phenyl)-2-methylpropanoyl chlorideHCID 23512644HCID 23512644, compound

Product 1

HCID 23512560HCID 23512560, compoundYield 58%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 0.70 g (2.6 mmol) [5-(2-Chloro-phenyl)-2-methylsulfanyl-pyrimidin-4-yl]-methyl-amine in 4 ml N,N-dimethylformamide 2.6 ml of a 1M solution potassiumhexamethyldisilazide (2.6 mmol) in THF were added at 0°. After 1 h, 0.92 g (2.6 mmol) (2-(3,5-bis-trifluoromethyl-phenyl)-2-methyl-propionyl chloride in 2 ml THF were added and the reaction mixture stirred for 24 hrs. at RT. The reaction mixture was poured onto 50 ml 0.5 N NaOH-solution. After addition of ethyl acetate the phases were separated, the aqueous layer washed twice with 50 ml ethyl acetate. The combined organic layers were dried (Na2SO4), filtered and evaporated. The residue was purified by chromatography (SiO2, CH2Cl2/ethyl acetate 19:1) to give 0.85 g (58%) 2-(3,5-bis-trifluoromethyl-phenyl)-N-[5-(2-chloro-phenyl)-2-methylsulfanyl-pyrimidin-4-yl]-N-methyl-isobutyramide as a white foam, MS (EI): 547 (M+).

Workup

  1. customat RT
  2. customwere separated
  3. washthe aqueous layer washed twice with 50 ml ethyl acetate
  4. dry with materialThe combined organic layers were dried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by chromatography (SiO2, CH2Cl2/ethyl acetate 19:1)

Sources & evidence

ORD record
ord-575be0a4a9e846589f46931c75439390
Source dataset
uspto-grants-2004_06
Patent number
US06756380B1

Reaction notes

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