Adenine → 9-[(Diethylphosphonomethoxy)methoxymethyl]adenine

HRID 1553

Reaction equation

[H-].[Na+].[N:3]1[C:11]([NH2:12])=[C:10]2[C:6]([N:7]=[CH:8][NH:9]2)=[N:5][CH:4]=1.Cl[CH2:14][O:15][CH2:16][O:17][CH2:18][P:19]([O:23][CH2:24][CH3:25])[O:20][CH2:21][CH3:22].C([O:28]P([O-])(OCC)=O)C.ClCOCOCCl>CN(C=O)C>[CH2:21]([O:20][P:19]([CH2:18][O:17][CH2:16][O:15][CH2:14][N:7]1[CH:8]=[N:9][C:10]2[C:6]1=[N:5][CH:4]=[N:3][C:11]=2[NH2:12])([O:23][CH2:24][CH3:25])=[O:28])[CH3:22]

Participants

Conditions

Temperature: 80 °C

Procedure

To a suspension of 60% sodium hydride in mineral oil (1.4 g, 34.5 mmol) in DMF (100 mL) was added adenine (4.7 g, 34.5 mmol) and the mixture was stirred at 80° C. for 1 hr. To the resulting yellow solution was added dropwise a solution of chloromethoxy(diethoxyphosphinomethoxy)methane [(prepared from diethylphosphate (4.4 mL, 34.5 mmol) and bis(chloromethoxy)methane (25 g, 172 mmol)] in DMF (20 mL) under nitrogen. After stirring at 25° C. for 15 hr, volatiles were removed in vacuo, and the resulting oily residue was purified by silica gel column chromatography using CH2Cl2 /10% MeOH as eluent to obtain the title compound as a colorless oil: yield 6.0 g (50%).

Workup

stirringAfter stirring at 25° C. for 15 hr
customvolatiles were removed in vacuo
customthe resulting oily residue was purified by silica gel column chromatography

Sources & evidence

ORD record: ord-93d03e24b2e64b579f6821175b3c99c2
Source dataset: uspto-grants-1998_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05726174

Linked notes

Loading…