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Pyridinium chloride → N-(4-(Dimethylphosphoryl)phenyl)-9-vinyl-9H-purin-6-amine

HRID 655794
Notes
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Reaction equation

HRID 655794 reaction equation
Cl[C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[CH:11]=[CH2:12].[CH3:13][P:14]([CH3:23])([C:16]1[CH:22]=[CH:21][C:19]([NH2:20])=[CH:18][CH:17]=1)=[O:15].Cl.N1C=CC=CC=1>C(OCCO)C>[CH3:23][P:14]([C:16]1[CH:22]=[CH:21][C:19]([NH:20][C:2]2[N:10]=[CH:9][N:8]=[C:7]3[C:3]=2[N:4]=[CH:5][N:6]3[CH:11]=[CH2:12])=[CH:18][CH:17]=1)([CH3:13])=[O:15]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 10176127Pyridinium chlorideHCID 109541366-Chloro-9-vinyl-9H-purineHCID 206345534-(Dimethylphosphoryl)aniline

Product 1

HCID 68925961N-(4-(Dimethylphosphoryl)phenyl)-9-vinyl-9H-purin-6-amine

Reagents, catalysts & solvents 1

HCID 8076Glycol monoethyl etherSolvent

Conditions

Temperature
160 °C

Procedure

A mixture of 6-chloro-9-vinylpurine (0.18 g, 1 mmol), 4-dimethylphosphinylaniline (0.17 g, 1 mmol), and pyridine hydrochloride (0.11 g, 1 mmol) was dissolved in 2-ethoxyethanol (2 mL). The resulting solution was heated at 160° C. for 10 minutes under microwave irradiation. The mixture was concentrated to dryness on a rotavap. EtOAc and aq. NaHCO3 were added. The aqueous layer was extracted with ethyl acetate and the combined organic layers were dried over sodium sulfate, concentrated on a rotavap, and then subjected to silica gel column chromatography (eluent: 10% methanol/methylene chloride) yielding the desired product.

Workup

  1. concentrationThe mixture was concentrated to dryness on a rotavap
  2. additionEtOAc and aq. NaHCO3 were added
  3. extractionThe aqueous layer was extracted with ethyl acetate
  4. dry with materialthe combined organic layers were dried over sodium sulfate
  5. concentrationconcentrated on a rotavap

Sources & evidence

ORD record
ord-02834ddfa82945d3bcfe0397c4dbb1f0
Source dataset
uspto-grants-2011_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08071609B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes