Bromotrimethylsilane → 2,6-Diamino-9-[1-hydroxy-3-(phosphonomethoxy)prop-2-oxy]purine

HRID 345083Notes

Reaction equation

[NH2:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[O:11][CH:12]([CH2:24][OH:25])[CH2:13][O:14][CH2:15][P:16]([O:21]CC)([O:18]CC)=[O:17])=[C:4]([NH2:26])[N:3]=1.Br[Si](C)(C)C>ClCCl>[NH2:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[O:11][CH:12]([CH2:13][O:14][CH2:15][P:16]([OH:21])([OH:18])=[O:17])[CH2:24][OH:25])=[C:4]([NH2:26])[N:3]=1

Participants

Conditions

Temperature: 20 °C

Procedure

To a solution of 2,6-diamino-9-[1-(diethoxyphosphorylmethoxy)-3-hydroxyprop-2-oxy]purine (100 mg, 0.26 mmol) in dichloromethane, was added bromotrimethylsilane (0.34 ml, 2.6 mmol) and the solution stirred under nitrogen for 4 h at 20° C. The solution was evaporated in vacuo and co-distilled with methanol and toluene. Recrystallisation of the residue with ethanol-water afforded 2,6-diamino-9-[1-hydroxy-3-(phosphonomethoxy)prop-2-oxy]purine (55 mg, 65%) as a white solid m.p. >300° C. decomp. λmax (H2O), 280 (ε10,100), 255 (ε8,400), 212 (ε26,100); νmax (KBr) 3360, 1700, 1660 and 1410 cm-1 ; δH (D2O+NH3) 3.55 (2H, m, CH2OH), 3.89 (4H, m, CH2OCH2P), 4.62 (1H, m, CHON), 8.10 (1 H, s, H-8). Found: C, 32.49; H, 4.63; N, 24.86%; C9H15N6O6P requires C, 32.34; H, 4.52; N, 25.14%.

Workup

customThe solution was evaporated in vacuo and co-distilled with methanol and toluene
customRecrystallisation of the residue with ethanol-water

Sources & evidence

ORD record: ord-9d454bb5525d45ecb4e7569d358a305b
Source dataset: uspto-grants-1991_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05055458

Reaction notes

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