Lithium iodide → HCID 67050495, compound

HRID 2194808Notes

Reaction equation

HRID 2194808 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([N:9]([C:13]2[NH:14][C:15](=[O:22])[NH:16][C:17](=[O:21])[C:18]=2[CH2:19][CH3:20])[C:10](=[O:12])[CH3:11])[CH:5]=[C:6]([CH3:8])[CH:7]=1.[I-].[Li+].CS([CH2:29]/[CH:30]=[CH:31]/[CH3:32])(=O)=O>CN(C=O)C.CCOCC>[CH2:29]([N:14]1[C:13]([N:9]([C:4]2[CH:3]=[C:2]([CH3:1])[CH:7]=[C:6]([CH3:8])[CH:5]=2)[C:10](=[O:12])[CH3:11])=[C:18]([CH2:19][CH3:20])[C:17](=[O:21])[NH:16][C:15]1=[O:22])[CH:30]=[CH:31][CH3:32]

Participants

6

Reactant 3

HCID 66321Lithium iodideHCID 15270286HCID 15270286, compoundHCID 21303242HCID 21303242, compound

Product 1

HCID 67050495HCID 67050495, compoundYield 40.9%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of N-(3,5-dimethyl-phenyl)-N-(5-ethyl-2,6-dioxo-1,2,3,6-tetrahydro-pyrimidin-4-yl)-acetamide (109) (602 mg, 2 mmol) anhydrous powdered K2CO3 (276 mg, 2 mmol), and lithium iodide (268 mg, 2 mmol) in DMF (6 mL), was added 1-methanesulfonyl-trans-2-butene (283 μL, 2.4 mmol). After stirring for 13 hr., the reaction mixture was diluted with ether, washed with water, dried with MgSO4, filtered, and evaporated in vacuo. The residue was purified by silica gel column chromatography (eluent, ethyl acetate:hexane (1:1)) to afford 291 mg (40%) of a white solid. m.p. 218-220° C.; m/z (EI) 355(M+).

Workup

  1. washwashed with water
  2. dry with materialdried with MgSO4
  3. filtrationfiltered
  4. customevaporated in vacuo
  5. customThe residue was purified by silica gel column chromatography (eluent, ethyl acetate:hexane (1:1))

Sources & evidence

ORD record
ord-712d6e4739d548d789f5093e715f9935
Source dataset
uspto-grants-2012_12
Patent number
US08334295B2

Reaction notes

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