Iodoethane → HCID 46880423, compound

HRID 2194803Notes

Reaction equation

HRID 2194803 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH:7]([C:10]1[C:15](=[O:16])[NH:14][C:13](=[O:17])[NH:12][C:11]=1[O:18][C:19]1[CH:20]=[C:21]([CH:24]=[C:25]([CH3:27])[CH:26]=1)[C:22]#[N:23])([CH3:9])[CH3:8].[CH2:28](I)[CH3:29].C(OCC)(=O)C>CN(C=O)C>[CH2:28]([N:12]1[C:11]([O:18][C:19]2[CH:20]=[C:21]([CH:24]=[C:25]([CH3:27])[CH:26]=2)[C:22]#[N:23])=[C:10]([CH:7]([CH3:9])[CH3:8])[C:15](=[O:16])[NH:14][C:13]1=[O:17])[CH3:29]

Participants

6

Reactant 4

HCID 6340IodoethaneHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 596868373-(5-Isopropyl-2,6-dioxo-1,2,3,6-tetrahydro-pyrimidin-4-yloxy)-5-methyl-benzonitrile

Product 1

HCID 46880423HCID 46880423, compoundYield 28%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Potassium carbonate (24 mg, 0.172 mmol, 1.0 eq.) was added to 3-(5-isopropyl-2,6-dioxo-1,2,3,6-tetrahydro-pyrimidin-4-yloxy)-5-methyl-benzonitrile (103) (59 mg, 0.207 mmol, 1.2 eq.) in 2.0 mL DMF. The reaction mixture was stirred at room temperature for 10 minutes, then ethyl iodide (14 μL, 0.172 mmol) was added. The reaction mixture was stirred at room temperature overnight. Ethyl acetate was added to the reaction mixture, which was then washed with brine. The organic layer was concentrated and purified (silica gel, 20-80% EtOAc/hexane), followed by reverse phase HPLC (MeCN/water) to give a white powder (15 mg, 28%). LC-MS shows 314.1 (M+1). 1H NMR (300 MHz, CDCl3): δ 9.17 (br, 1H), 7.25 (s, 1H), 7.08 (s, 1H), 7.00 (s, 1H), 3.77 (t, 2H), 2.69 (m, 1H), 2.42 (s, 3H), 1.2 (m, 9H).

Workup

  1. stirringThe reaction mixture was stirred at room temperature overnight
  2. washwas then washed with brine
  3. concentrationThe organic layer was concentrated
  4. custompurified (silica gel, 20-80% EtOAc/hexane)

Sources & evidence

ORD record
ord-ae31bbeb744a4b03aebee73cdda78485
Source dataset
uspto-grants-2012_12
Patent number
US08334295B2

Reaction notes

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