Methyl iodide → HCID 86591949, compound

HRID 1792076Notes

Reaction equation

HRID 1792076 reaction equation
[H-].[Na+].[C:3]([O:7][C:8]([N:10]1[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12][CH:11]1[CH:23]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[N:31]1[C:39]2[C:38](=[O:40])[N:37]([CH3:41])[C:36](=[O:42])[N:35]([CH3:43])[C:34]=2[N:33]=[CH:32]1)[OH:24])=[O:9])([CH3:6])([CH3:5])[CH3:4].[C:44](=[S:46])=[S:45].[CH3:47]I>O1CCCC1.O.C(OCC)(=O)C>[C:3]([O:7][C:8]([N:10]1[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12][CH:11]1[CH:23]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[N:31]1[C:39]2[C:38](=[O:40])[N:37]([CH3:41])[C:36](=[O:42])[N:35]([CH3:43])[C:34]=2[N:33]=[CH:32]1)[O:24][C:44]([S:46][CH3:47])=[S:45])=[O:9])([CH3:4])([CH3:5])[CH3:6]

Participants

8

Reactant 4

HCID 6328Methyl iodideHCID 6348Carbon DisulfideHCID 24758Sodium hydrideHCID 23536895HCID 23536895, compound

Product 1

HCID 86591949HCID 86591949, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Sodium hydride (60% oleaginous) was added to a solution of 2-[[2-(1,3-dimethyl-2,6-dioxo-1,2,3,6-tetrahydropurin-7-yl)-phenyl]hydroxymethyl]piperazine-1,4-dicarboxylic acid di-tert-butyl ester (low polarity) (0.214 g) in tetrahydrofuran (10 ml) at 0° C. under nitrogen atmosphere, and the mixture was stirred at room temperature for 20 minutes. The temperature of the mixture was returned to 0° C., carbon disulfide (0.045 ml) was added thereto, and the mixture was stirred for 1 hour. Then, methyl iodide (0.047 ml) was added to the reaction mixture, and the mixture was further stirred at room temperature for 2 hours. The reaction mixture was poured into 50 ml of ethyl acetate and 20 ml of water, the organic layer was dried over anhydrous magnesium sulfate, and the solvent was removed by distillation at reduced pressure. The residue was purified by silica gel column chromatography to give 0.175 g of the title compound from the elution fraction of hexane-ethyl acetate (3:7).

Workup

  1. customwas returned to 0° C.
  2. stirringthe mixture was stirred for 1 hour
  3. stirringthe mixture was further stirred at room temperature for 2 hours
  4. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  5. customthe solvent was removed by distillation at reduced pressure
  6. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-469fd5b0efd24e2eb3d5f6ee45439c61
Source dataset
uspto-grants-2006_07
Patent number
US07074798B2

Reaction notes

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