Diisopropylethylamine → HCID 11524223, compound

HRID 1744798Notes

Reaction equation

HRID 1744798 reaction equation
Cl[C:2]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[C:6]([CH3:13])[N:5]=[C:4]([S:14][CH3:15])[N:3]=1.[NH2:16][C:17]1[CH:29]=[CH:28][C:20]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])=[CH:19][CH:18]=1.C(N(CC)C(C)C)(C)C>O1CCOCC1>[C:24]([O:23][C:21]([C:20]1[CH:19]=[CH:18][C:17]([NH:16][C:2]2[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[C:6]([CH3:13])[N:5]=[C:4]([S:14][CH3:15])[N:3]=2)=[CH:29][CH:28]=1)=[O:22])([CH3:27])([CH3:25])[CH3:26]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 233272Benzoic acid, 4-amino-, 1,1-dimethylethyl esterHCID 22225416Ethyl 4-chloro-6-methyl-2-(methylsulfanyl)pyrimidine-5-carboxylate

Product 1

HCID 11524223HCID 11524223, compoundYield 81.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of compound D (31.5 g; 0.1278 mol), tert-butyl 4-aminobenzoate (48 g; 0.248 mol), N,N-diisopropylethylamine (50.3 g; 0.39 mol) in 400 mL of dioxane was refluxed for 72 h under magnetic stirring. The reaction mixture was filtered, concentrated and taken up with ethyl acetate. The organic phase was washed with water and brine, dried over anhydrous sodium sulphate and concentrated. The crude mixture was purified by silica gel column chromatography (eluant: n-hexane/ethyl acetate=9/1) to yield compound E (41.8 g; 81%).

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated
  3. washThe organic phase was washed with water and brine
  4. dry with materialdried over anhydrous sodium sulphate
  5. concentrationconcentrated
  6. customThe crude mixture was purified by silica gel column chromatography (eluant: n-hexane/ethyl acetate=9/1)

Sources & evidence

ORD record
ord-5c8c4559977347078301f89b97a38284
Source dataset
uspto-grants-2006_03
Patent number
US07019002B2

Reaction notes

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