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

HRID 655794Notes

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]

Participants

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

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

Loading…