Potassium Carbonate → Diethyl 4-{7-[4-(diethoxyphosphoryl)butyl]-3-methylxanthin-1-yl}butyl-phosphonate

HRID 1999Notes

Reaction equation

[CH2:1]([O:3][P:4]([CH2:9][CH2:10][CH2:11][CH2:12][N:13]1[C:21]2[C:20](=[O:22])[NH:19][C:18](=[O:23])[N:17]([CH3:24])[C:16]=2[N:15]=[CH:14]1)([O:6][CH2:7][CH3:8])=[O:5])[CH3:2].Cl[CH2:26][CH2:27][CH2:28][CH2:29][P:30]([O:35][CH2:36][CH3:37])(=[O:34])[O:31][CH2:32][CH3:33].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH2:7]([O:6][P:4]([CH2:9][CH2:10][CH2:11][CH2:12][N:13]1[C:21]2[C:20](=[O:22])[N:19]([CH2:26][CH2:27][CH2:28][CH2:29][P:30](=[O:34])([O:35][CH2:36][CH3:37])[O:31][CH2:32][CH3:33])[C:18](=[O:23])[N:17]([CH3:24])[C:16]=2[N:15]=[CH:14]1)([O:3][CH2:1][CH3:2])=[O:5])[CH3:8]

Participants

Conditions

Temperature: 70 °C

Procedure

8 g (0.022 mol) of 7-(4-diethylphosphonobutyl)-3-methylxanthine (according to Example 24) were suspended in 100 ml of DMF, treated with 6.13 g (0.027 mol) of diethyl 4-chlorobutanephosphonate and 3.7 g (0.028 mol) of activated potassium carbonate and heated at 70° C. for 4 hours. The product was then filtered, the filtrate was concentrated under reduced pressure and the oily residue which remained was chromatographed on a silica gel column (eluent: ethyl acetate/methanol 10:1).

Workup

filtrationThe product was then filtered
concentrationthe filtrate was concentrated under reduced pressure
customthe oily residue which remained was chromatographed on a silica gel column (eluent: ethyl acetate/methanol 10:1)

Sources & evidence

ORD record: ord-c12104568b5442eda2e049aa7fbffb8a
Source dataset: uspto-grants-1998_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05728686

Reaction notes

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