Acetic Acid → HCID 60204316, compound

HRID 2267308Notes

Reaction equation

HRID 2267308 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:13]=[CH:12][N:11]=[C:10]([NH:14][CH2:15][CH2:16][N:17]3[C:21]([CH3:23])([CH3:22])[C:20](=[O:24])[NH:19][C:18]3=[O:25])[N:9]=2)[S:5][C:6]=1[Cl:7].CO.C(O)(=O)C.[Br:32]Br>ClCCl>[Br:32][C:13]1[C:8]([C:4]2[S:5][C:6]([Cl:7])=[C:2]([Cl:1])[CH:3]=2)=[N:9][C:10]([NH:14][CH2:15][CH2:16][N:17]2[C:21]([CH3:22])([CH3:23])[C:20](=[O:24])[NH:19][C:18]2=[O:25])=[N:11][CH:12]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 887MethanolHCID 24408BromineHCID 60204300HCID 60204300, compound

Product 1

HCID 60204316HCID 60204316, compoundYield 73.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-(2-(4-(4,5-Dichlorothiophen-2-yl)pyrimidin-2-ylamino)ethyl)-5,5-dimethyl imidazolidine-2,4-dione (300 mg, 0.75 mmol) was suspended in a 10% solution of methanol in dichloromethane (7 mL). Glacial acetic acid (1 mL) followed by bromine (120 mg, 0.75 mmol, 39 μL) [material immediately went into solution] were added, and the mixture was stirred at room temperature for 3 h. The reaction was concentrated in vacuo, diluted with deionized water (25 mL), stirred for 5 min, and then the product was collected by filtration to give a yellow solid (265 mg). The crude product was purified by flash chromatography (MeOH/DCM) to yield the title compound as a yellow powder (162 mg, 45%). MS (M+H)+ 478/480.

Workup

  1. additionwere added
  2. concentrationThe reaction was concentrated in vacuo
  3. additiondiluted with deionized water (25 mL)
  4. stirringstirred for 5 min
  5. filtrationthe product was collected by filtration

Sources & evidence

ORD record
ord-a674079645b14e4493bb0e48954848ad
Source dataset
uspto-grants-2010_12
Patent number
US07858785B2

Reaction notes

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