Diisopropylethylamine → HCID 178469437, compound

HRID 1666157Notes

Reaction equation

HRID 1666157 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([F:11])=[CH:7][CH:6]=1)=O.C(N(C(C)C)C(C)C)C.[CH2:21]([O:23][C:24]([C:26]1[C:27]([OH:33])=[N:28][C:29]([NH2:32])=[N:30][CH:31]=1)=[O:25])[CH3:22]>O1CCOCC1>[CH2:21]([O:23][C:24]([C:26]1[C:27]([OH:33])=[N:28][C:29]2[N:30]([CH:2]=[C:3]([C:5]3[CH:10]=[CH:9][C:8]([F:11])=[CH:7][CH:6]=3)[N:32]=2)[CH:31]=1)=[O:25])[CH3:22]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 967492-Bromo-1-(4-fluorophenyl)ethan-1-oneHCID 178469836HCID 178469836, compound

Product 1

HCID 178469437HCID 178469437, compoundYield 4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

2-Bromo-1-(4-fluoro-phenyl)ethanone (200.1 mg, 0.922 mmol), ethyl-diisopropylamine (160.6 μl, 0.922 mmol) and 2-amino-4-hydroxy-pyrimidine-5-carboxylic acid ethyl ester (168.9 mg, 0.922 mmol) were heated under reflux in 50 ml dioxane for 8.5 hours. The mixture was evaporated. Ethyl acetate and water were added, the organic layer was separated, washed with water, dried and evaporated. The crude product was purified by preparative HPLC (RP18, acetonitrile/water 0.1% TFA) to yield 11 mg (4%) of the desired product. MS (mass spectrum): M+H+=302.11.

Workup

  1. customThe mixture was evaporated
  2. additionEthyl acetate and water were added
  3. customthe organic layer was separated
  4. washwashed with water
  5. customdried
  6. customevaporated
  7. customThe crude product was purified by preparative HPLC (RP18, acetonitrile/water 0.1% TFA)

Sources & evidence

ORD record
ord-649a172fc6cd4ff7afe7263dfe578bfe
Source dataset
uspto-grants-2011_10
Patent number
US08044050B2

Reaction notes

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