Formic Acid → 9-[4-(Diethoxyphosphoryl)butoxy]guanine

HRID 373905Notes

Reaction equation

HRID 373905 reaction equation
Cl[C:2]1[N:10]=[C:9]([NH:11]C=O)[N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[O:14][CH2:15][CH2:16][CH2:17][CH2:18][P:19]([O:24][CH2:25][CH3:26])([O:21][CH2:22][CH3:23])=[O:20].C(O)=[O:28]>>[CH2:22]([O:21][P:19]([CH2:18][CH2:17][CH2:16][CH2:15][O:14][N:6]1[CH:5]=[N:4][C:3]2[C:2](=[O:28])[NH:10][C:9]([NH2:11])=[N:8][C:7]1=2)([O:24][CH2:25][CH3:26])=[O:20])[CH3:23]

Participants

3

Reactant 2

HCID 284Formic AcidHCID 198086486-Chloro-9-[4-(diethoxyphosphoryl)butoxy]-2-formamidopurine

Product 1

HCID 1360386719-[4-(Diethoxyphosphoryl)butoxy]guanineYield 76%

Procedure

A solution of 6-chloro-9-[4-(diethoxyphosphoryl)butoxy]-2-formamidopurine (0.220 g, 0.54 mmol) in 80% formic acid (5 ml) was stirred at 80° C. for 5 hr. The solvent was evaporated under vacuum and the residue coevaporated with toluene (2×10 ml). The residue was chromatographed on silica gel (eluted with chloroform-ethanol 9:1) to give the title compound (0.148 g, 76%). 1H NMR: δH ((CD3)2SO) 1.22 (6H, t, J=7 Hz, (OCH2CH3)2), 1.64 (2H, m, CH2P), 1.79 (4H, m, CH2CH2), 3.9 (4H, m, (OCH2CH3)2), 4.26 (2H, t, NOCH2), 6.67 (2H, br.s, D2O exchangeable, NH2), 7.96 (1H, s, H-8), 10.75 (1H, br.s, D2O exchangeable, NH).

Workup

  1. customThe solvent was evaporated under vacuum
  2. customThe residue was chromatographed on silica gel (eluted with chloroform-ethanol 9:1)

Sources & evidence

ORD record
ord-0721078e36f04a9b8b8b6b1b84a50abd
Source dataset
uspto-grants-1992_11
Patent number
US05166198

Reaction notes

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