Sodium Hydroxide → HCID 21712473, compound

HRID 650640Notes

Reaction equation

HRID 650640 reaction equation
[CH3:1][NH:2][C:3]1[C:4]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[CH3:17])=[N:5][C:6]([S:9][CH3:10])=[N:7][CH:8]=1.C(N(C(C)C)C(C)C)C.[F:27][C:28]([F:46])([F:45])[C:29]1[CH:30]=[C:31]([C:39]([CH3:44])([CH3:43])[C:40](Cl)=[O:41])[CH:32]=[C:33]([C:35]([F:38])([F:37])[F:36])[CH:34]=1.[OH-].[Na+]>C(Cl)Cl>[F:27][C:28]([F:46])([F:45])[C:29]1[CH:30]=[C:31]([C:39]([CH3:44])([CH3:43])[C:40]([N:2]([CH3:1])[C:3]2[C:4]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[CH3:17])=[N:5][C:6]([S:9][CH3:10])=[N:7][CH:8]=2)=[O:41])[CH:32]=[C:33]([C:35]([F:38])([F:37])[F:36])[CH:34]=1

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 81531DiisopropylethylamineHCID 112671412-(3,5-Bis(trifluoromethyl)phenyl)-2-methylpropanoyl chlorideHCID 23512569HCID 23512569, compound

Product 1

HCID 21712473HCID 21712473, compoundYield 82.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 1.30 g (5.3 mmol) methyl-(2-methylsulfanyl-4-o-tolyl-pyrimidin-5-yl)-amine and 1.36 ml (7.95 mmol) N-ethyldiisopropylamine in 15 ml CH2Cl2 a solution of 1.30 g (5.3 mmol) 2-(3,5-bis-trifluoromethyl-phenyl)-2-methyl-propionyl chloride in 5 ml CH2Cl2 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. The phases were separated, the aqueous layer washed twice with 50 ml CH2Cl2. The combined organic layers were dried (Na2SO4), filtered and evaporated. The residue was purified by chromatography (SiO2, CH2Cl2/ethyl acetate 10:1) to give 2.30 g (82%) 2-(3,5-bis-trifluoromethyl-phenyl)-N-methyl-N-(2-methylsulfanyl-4-o-tolyl-pyrimidin-5-yl)-isobutyramide as a white solid, m.p. 124-125°, MS (ISP): 528.2 (M+H+).

Workup

  1. customat RT
  2. customThe phases were separated
  3. washthe aqueous layer washed twice with 50 ml CH2Cl2
  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 10:1)

Sources & evidence

ORD record
ord-453bf4a8b9ed44318171912397b5fe11
Source dataset
uspto-grants-2001_08
Patent number
US06274588B1

Reaction notes

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