Ammonia → HCID 178468218, compound

HRID 2180221Notes

Reaction equation

HRID 2180221 reaction equation
O[CH2:2][CH2:3][O:4][CH2:5][N:6]1[CH:14]=[N:13][C:12]2[C:11](=[O:15])[NH:10][C:9]([NH2:16])=[N:8][C:7]1=2.[H-].[Na+].[CH3:19][CH:20]([CH3:26])[CH2:21][C:22](=O)[CH2:23]Br.N.CN(C)C=[O:31]>>[OH:31][C:14]1[N:6]([CH2:5][O:4][CH2:3][CH3:2])[C:7]2[N:8]=[C:9]3[N:10]([CH:23]=[C:22]([CH2:21][CH:20]([CH3:26])[CH3:19])[NH:16]3)[C:11](=[O:15])[C:12]=2[N:13]=1

Participants

6

Reactant 5

HCID 222AmmoniaHCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 110844641-Bromo-4-methyl-2-pentanoneHCID 135398513Acyclovir

Product 1

HCID 178468218HCID 178468218, compound

Procedure

A solution of 676 mg a 9-[(2-hydroxyethoxy)methyl]guanine (acyclovir), 18 mL N,N-dimethylformamide (DMF), and 200 mg sodium hydride (80%) was stirred at room temperature for 15 min, then 0.7 mL 4-methyl-1-bromopentan-2-one was added dropwise into the solution. Changing to dark-brown color, the solution was stirred at room temperature for 3 hr, added 15 mL ammonia, and was continuously stirred overnight. The solvent was removed to obtain a residue, which was purified by column chromatography (silica gel) with an elute of chloroform/methanol (6/1) to obtain an oil. Recrystallization of the oil produced compound 1.

Workup

  1. waitwas continuously stirred overnight
  2. customThe solvent was removed
  3. customto obtain a residue, which
  4. customwas purified by column chromatography (silica gel) with
  5. washan elute of chloroform/methanol (6/1)
  6. customto obtain an oil
  7. customRecrystallization of the oil

Sources & evidence

ORD record
ord-5e3fb2292dc34252b5937ba68c635184
Source dataset
uspto-grants-2005_05
Patent number
US06887997B2

Reaction notes

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