Diisopropylethylamine → HCID 178473679, compound

HRID 1241345Notes

Reaction equation

Cl[C:2]1[N:10]=[C:9]([I:11])[N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[CH:12]([CH3:14])[CH3:13].[CH2:15]([O:17][P:18]([C:23]([C:29]1[CH:34]=[CH:33][C:32]([NH2:35])=[CH:31][CH:30]=1)([O:26][CH2:27][CH3:28])[PH2:24]=[O:25])(=[O:22])[O:19][CH2:20][CH3:21])[CH3:16].CCN(C(C)C)C(C)C>CCO>[CH2:15]([O:17][P:18]([C:23]([O:26][CH2:27][CH3:28])([C:29]1[CH:30]=[CH:31][C:32]([NH:35][C:2]2[N:10]=[C:9]([I:11])[N:8]=[C:7]3[C:3]=2[N:4]=[CH:5][N:6]3[CH:12]([CH3:14])[CH3:13])=[CH:33][CH:34]=1)[PH2:24]=[O:25])(=[O:22])[O:19][CH2:20][CH3:21])[CH3:16]

Participants

Conditions

Temperature: 105 °C

Procedure

6-Chloro-2-iodo-9-isopropyl-9H-purine (1.7 g, 5.2 mmol), [(4-amino-phenyl)-ethoxy-phosphinoylmethyl]-phosphonic acid diethyl ester (2.6 g, 7.7 mmol), and DIPEA (2.7 mL, 15.5 mmol) were dissolved in EtOH (27 mL) and heated in a sealed tube at 105° C. for 48 h. After cooling, the EtOH was evaporated. The residue was poured into water and extracted with EtOAc. The combined extracts, were washed with water, sat'd NaCl, then dried over MgSO4 and filtered. Concentration yielded an oil which was purified by silica gel chromatography (11% MeOH/EtOAc) to a glassy solid (1.8 g, 53%): MS [M+H]+ 621.

Workup

temperatureAfter cooling
customthe EtOH was evaporated
additionThe residue was poured into water
extractionextracted with EtOAc
washThe combined extracts, were washed with water
dry with materialdried over MgSO4
filtrationfiltered
concentrationConcentration
customyielded an oil which
customwas purified by silica gel chromatography (11% MeOH/EtOAc) to a glassy solid (1.8 g, 53%)

Sources & evidence

ORD record: ord-fcbec09b697940fa82de85ecb45d114d
Source dataset: uspto-grants-2006_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07115589B2

Reaction notes

Loading…