Methanol → 2-[(6-aminopurin-9-yl)methoxy]ethylphosphonic acid

HRID 3085Notes

Reaction equation

[N:1]1[C:9]([NH2:10])=[C:8]2[C:4]([N:5]([CH2:11][O:12][CH2:13][CH2:14][P:15](=[O:20])([O-:19])[O:16]CC)[CH:6]=[N:7]2)=[N:3][CH:2]=1.[NH4+].CO.O>CN(C=O)C>[N:1]1[C:9]([NH2:10])=[C:8]2[C:4]([N:5]([CH2:11][O:12][CH2:13][CH2:14][P:15](=[O:16])([OH:19])[OH:20])[CH:6]=[N:7]2)=[N:3][CH:2]=1

Participants

Conditions

Temperature: 40 °C

Procedure

To a solution of 12 (0.32 g, 1.0 mmol) in DMF (7.0 mL) was added Me3 SiBr (1.07 g, 7.01 mmol). After the solution was stirred at 40° C. for 6 h, a mixture of MeOH and H2O(5:1, 20 mL) was added and the solvents were evaporated. The crude residue was purified by use of column chromatography (resin XAD-4, H2O) to afford 13 (0.12 g, 45%): mp 296° C. (dec.); TLC Rf 0.32 (MeOH); UV λmax (EtOH): 259 nm (ε13 700); 1H NMR(DMSO-d6 /D2O): δ1.49 (m, 2 H, CH2P), 3.80 (m, 2 H, CH2O), 5.55 (s, 2 H, OCH2 N), 7.90, 8.19 (2 s, 2 H, HC(2)+HC(8)). Anal. (C8H12N5 O4P) C, H, N.

Workup

additionwas added
customthe solvents were evaporated
customThe crude residue was purified by use of column chromatography (resin XAD-4, H2O)

Sources & evidence

ORD record: ord-665b5ee29c834289ad987373eaa9f519
Source dataset: uspto-grants-1998_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05733890

Reaction notes

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