Bromotrimethylsilane → 9-(4-Phosphonobutoxy)guanine

HRID 373904Notes

Reaction equation

C([O:3][P:4]([CH2:9][CH2:10][CH2:11][CH2:12][O:13][N:14]1[CH:22]=[N:21][C:20]2[C:19](=[O:23])[NH:18][C:17]([NH2:24])=[N:16][C:15]1=2)([O:6]CC)=[O:5])C.Br[Si](C)(C)C>CN(C)C=O>[P:4]([CH2:9][CH2:10][CH2:11][CH2:12][O:13][N:14]1[CH:22]=[N:21][C:20]2[C:19](=[O:23])[NH:18][C:17]([NH2:24])=[N:16][C:15]1=2)([OH:5])([OH:6])=[O:3]

Participants

Conditions

Temperature: 23 °C

Procedure

9-[4-(Diethoxyphosphoryl)butoxy]guanine (0.12 g, 0.33 mmol) and bromotrimethylsilane (0.43 ml, 3.3 mmol) were dissolved in dimethylformamide (5 ml) and the reaction mixture was stirred at 23° C. for 3 hr. The solvent was evaporated under vacuum and the residue dissolved in methanol:water solution (9:1). The pH of the resulting solution was adjusted to 7.0 with diluted aq. ammonia and the solvents were evaporated to dryness. The product was purified by reversed phase chromatography (eluted with water) to give the title compound (65 mg, 64%) m.p. 208° C. (water), as its ammonium salt. 1H NMR: δH ((CD3)2, SO+D2O) 1.40 (2H, m, CH2P), 1.68 (4H, br.s, CH2CH2), 4.21 (2H, m, NOCH2), 7.89 (1H, s, H-8).

Workup

customThe solvent was evaporated under vacuum
dissolutionthe residue dissolved in methanol
customthe solvents were evaporated to dryness
customThe product was purified by reversed phase chromatography (eluted with water)

Sources & evidence

ORD record: ord-cb72c9956e6f4377bc53dae651f93ba3
Source dataset: uspto-grants-1992_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05166198

Reaction notes

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