Sodium Iodide → HCID 86588149, compound

HRID 1828538Notes

Reaction equation

HRID 1828538 reaction equation
O(P(O[C:18]1[N:19]=[C:20]2[CH:37]=[C:36]([CH2:38][CH2:39][C:40]3[S:41][CH:42]=[C:43]([CH:45]([CH3:47])[CH3:46])[N:44]=3)[CH:35]=[CH:34][N:21]2[C:22](=[O:33])[C:23]=1/[CH:24]=[CH:25]/[C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])(OC1C=CC=CC=1)=O)C1C=CC=CC=1.[S-2:48].[Li+].[Li+].Br[CH2:52][C:53]([O:55][C:56]([CH3:59])([CH3:58])[CH3:57])=[O:54].[I-].[Na+]>CN(C)C=O.C(O)C.O.C(OCC)(=O)C>[C:56]([O:55][C:53]([CH2:52][S:48][C:18]1[N:19]=[C:20]2[CH:37]=[C:36]([CH2:38][CH2:39][C:40]3[S:41][CH:42]=[C:43]([CH:45]([CH3:46])[CH3:47])[N:44]=3)[CH:35]=[CH:34][N:21]2[C:22](=[O:33])[C:23]=1/[CH:24]=[CH:25]/[C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])=[O:54])([CH3:59])([CH3:58])[CH3:57]

Participants

9

Reactant 4

HCID 5238Sodium IodideHCID 79177tert-Butyl bromoacetateHCID 10290727Dilithium SulfideHCID 131725784HCID 131725784, compound2×

Product 1

HCID 86588149HCID 86588149, compound

Reagents, catalysts & solvents 4

HCID 702EthanolSolventHCID 962WaterSolventHCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

The tert-butyl (E)-3-{2-[(diphenoxyphosphoryl)oxy]-8-[2-(4-isopropyl-1,3-thiazol-2-yl)ethyl]-4-oxo-4H-pyrido[1,2-a]pyrimidin-3-yl}-2-propenoate (62 mg) obtained in (A) was dissolved in dimethylformamide (1 ml) and added dropwise with a solution of lithium sulfide in ethanol (0.1 g/ml) until the starting material disappeared. Separately, tert-butyl bromoacetate (0.04 ml) was dissolved in dimethylformamide (1 ml), added with sodium iodide (69 mg), and then stirred at room temperature for 40 minutes. These two of solutions were mixed and stirred at room temperature for 2 hours. The reaction mixture was distributed between ethyl acetate and water, and the organic layer was dried. The solvent was evaporated, and the residue was purified by silica gel column chromatography to obtain the title compound (19 mg).

Workup

  1. additionThese two of solutions were mixed
  2. stirringstirred at room temperature for 2 hours
  3. customthe organic layer was dried
  4. customThe solvent was evaporated
  5. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-895628a6f2574486a99a40e59a6462bd
Source dataset
uspto-grants-2006_06
Patent number
US07056917B2

Reaction notes

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