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Water → HCID 22007318, compound

HRID 323876
Notes
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Reaction equation

HRID 323876 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH3:7][N:8]1[C:16]2[N:15]=[CH:14][N:13]([C:17]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:12]=2[C:11](=[O:36])[NH:10][C:9]1=[O:37].[CH2:38]([O:45][CH2:46]Cl)[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1.O>CN(C)C=O>[CH2:38]([O:45][CH2:46][N:10]1[C:11](=[O:36])[C:12]2[N:13]([C:17]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)([C:30]3[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=3)[C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH:14]=[N:15][C:16]=2[N:8]([CH3:7])[C:9]1=[O:37])[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 137983Benzyl chloromethyl etherHCID 22007310HCID 22007310, compound

Product 1

HCID 22007318HCID 22007318, compound

Reagents, catalysts & solvents 1

HCID 6228Dimethylformamide
Solvent

Procedure

1.3 g (9.44 mmol) of potassium carbonate were added at 60° C. to a solution of 2.4 g (5.9 mmol) of 3-methyl-7-tritylxanthine from stage a) in 50 ml of dimethylformamide and the mixture was stirred at this temperature for one hour. 1.06 ml (7.67 mmol) of benzyloxymethyl chloride were then added dropwise and the mixture was stirred at 80° C. for 7 hours. 50 ml of water were then added and the mixture was extracted three times using 60 ml of methyl tert-butyl ether each time. The combined organic phases were washed twice with 30 ml of water each time, dried using magnesium sulfate and concentrated under reduced pressure. The crude product was purified by flash chromatography on a silica gel column, heptane/ethyl acetate (3/2).

Workup

  1. stirringthe mixture was stirred at 80° C. for 7 hours
  2. extractionthe mixture was extracted three times
  3. washThe combined organic phases were washed twice with 30 ml of water each time
  4. customdried
  5. concentrationconcentrated under reduced pressure
  6. customThe crude product was purified by flash chromatography on a silica gel column, heptane/ethyl acetate (3/2)

Sources & evidence

ORD record
ord-43c493a903f4471eb3efe46a36545df3
Source dataset
uspto-grants-2001_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06214992B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes