Sodium Hydroxide → HCID 10165878, compound

HRID 1005983Notes

Reaction equation

HRID 1005983 reaction equation
[CH3:1][NH:2][C:3]1[C:4]([O:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[CH3:18])=[N:5][C:6]([S:9][CH3:10])=[N:7][CH:8]=1.C(N(C(C)C)C(C)C)C.[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+]>C(Cl)Cl>[F:28][C:29]([F:47])([F:46])[C:30]1[CH:31]=[C:32]([C:40]([CH3:45])([CH3:44])[C:41]([N:2]([CH3:1])[C:3]2[C:4]([O:11][C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[CH3:18])=[N:5][C:6]([S:9][CH3:10])=[N:7][CH:8]=2)=[O:42])[CH:33]=[C:34]([C:36]([F:39])([F:38])[F:37])[CH:35]=1

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 81531DiisopropylethylamineHCID 112671412-(3,5-Bis(trifluoromethyl)phenyl)-2-methylpropanoyl chlorideHCID 22674310HCID 22674310, compound

Product 1

HCID 10165878HCID 10165878, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 1.10 g (4.21 mol) methyl-(2-methylsulfanyl-4-o-tolyloxy-pyrimidin-5-yl)-amine and 1.44 ml (8.42 mmol) N-ethyldiisopropylamine in 30 ml CH2Cl2 a solution of 1.87 g (5.89 mmol) 2-(3,5-bis-trifluormethyl-phenyl)-2-methyl-propionyl chloride in 5 ml CH2Cl2 was added and the reaction mixture stirred for 12 hrs at RT. The reaction mixture was poured into 50 ml 0.5 N NaOH-solution. The phases were separated and the aqueous phase three times extracted with 80 ml CH2Cl2. The combined organic layers were dried (Na2SO4), filtered and evaporated. The residue was purified by chromatography (SiO2, hexane/ ethyl acetate 2:1) to give 2.10 g (92%) 2-(3,5-bis-trifluoromethyl-phenyl)-N-methyl-N-(2-methylsulfanyl-4-o-tolyloxy-pyrimidin-5-yl)-isobutyramide as a white foam, MS (ISP): 544.2 (M+H)+.

Workup

  1. customThe phases were separated
  2. extractionthe aqueous phase three times extracted with 80 ml CH2Cl2
  3. dry with materialThe combined organic layers were dried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified by chromatography (SiO2, hexane/ ethyl acetate 2:1)

Sources & evidence

ORD record
ord-d54abdec8f0e47a8818aff6e7bfb61b3
Source dataset
uspto-grants-2004_09
Patent number
US06787539B2

Reaction notes

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