N,N-Dimethylaniline → HCID 178491704, compound

HRID 2276297Notes

Reaction equation

HRID 2276297 reaction equation
O[C:2]1[N:10]=[C:9]([S:11][CH2:12][C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[C:15]([N+:21]([O-:23])=[O:22])[CH:14]=2)[N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][NH:6]2.P(Cl)(Cl)([Cl:26])=O.CN(C)C1C=CC=CC=1>O1CCOCC1>[Cl:26][C:2]1[N:10]=[C:9]([S:11][CH2:12][C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[C:15]([N+:21]([O-:23])=[O:22])[CH:14]=2)[N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][NH:6]2

Participants

5

Reactant 3

HCID 949N,N-DimethylanilineHCID 24813Phosphorus oxychlorideHCID 178491707HCID 178491707, compound

Product 1

HCID 178491704HCID 178491704, compoundYield 35.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

6-hydroxy-2-(4-methoxy-3-nitrobenzylsulfanyl)-9H-purine (14.67 g, 44 mmol) was suspended in dioxane (30 ml), phosphorus oxychloride (12.3 ml, 132 mmol) and dimethylaniline (8.3 ml, 66 mmol) were added and heated and stirred at 100° C. for 2 hours. The reaction solution was poured into ice water and extracted twice with ethyl acetate. After combining the ethyl acetate layers and washing with a saturated saline solution, it was dried with MgSO4 and the solvent was distilled away under reduced pressure. Separation and purification were performed by silica gel column chromatography (dichloromethane: methanol=20:1) to obtain 5.45 g (35% yield) of 6-chloro-2-(4-methoxy-3-nitrobenzylsulfanyl)-9H-purine.

Workup

  1. temperatureheated
  2. extractionextracted twice with ethyl acetate
  3. washwashing with a saturated saline solution, it
  4. dry with materialwas dried with MgSO4
  5. distillationthe solvent was distilled away under reduced pressure
  6. customSeparation and purification

Sources & evidence

ORD record
ord-414961162d7c4170b98ec790ca90e1ef
Source dataset
uspto-grants-2015_09
Patent number
US09132130B2

Reaction notes

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