Formic Acid → 9-[3-(Diethoxyphosphorylmethoxy)propoxy]guanine

HRID 345073Notes

Reaction equation

HRID 345073 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][O:18][CH2:19][P:20]([O:25][CH2:26][CH3:27])([O:22][CH2:23][CH3:24])=[O:21].C(O)=[O:29]>>[CH2:23]([O:22][P:20]([CH2:19][O:18][CH2:17][CH2:16][CH2:15][O:14][N:6]1[CH:5]=[N:4][C:3]2[C:2](=[O:29])[NH:10][C:9]([NH2:11])=[N:8][C:7]1=2)([O:25][CH2:26][CH3:27])=[O:21])[CH3:24]

Participants

3

Reactant 2

HCID 284Formic AcidHCID 199935066-Chloro-9-[3-(diethoxyphosphorylmethoxy)propoxy]-2-formamidopurine

Product 1

HCID 1359874429-[3-(Diethoxyphosphorylmethoxy)propoxy]guanineYield 52%

Conditions

Temperature
25 °C

Procedure

6-Chloro-9-[3-(diethoxyphosphorylmethoxy)propoxy]-2-formamidopurine (1.5 g, 3.56 mmol) was heated at 100° C. for 2 h in 80% formic acid (15 ml) then evaporated under reduced pressure. The residue was taken up in methanol (15 ml) and 0.88 ammonia (15 ml) and stirred at 25° C. for 1 h then evaporated to dryness. Precipitation from hot water afforded 9-[3-(diethoxyphosphorylmethoxy)propoxy]guanine (0.69 g, 52%) as a pale yellow solid; νmax 3335, 1694, 1475, 1390, 1249, 1026 cm-1 ; δH [(CD3)2SO] 1.22(6H, t, J7 Hz, (CH3CH2O)2), 1.90(2H, m, CH2CH2CH2), 3.68(2H, t, J6 Hz, CH2OCH2P), 3.83(2H, d, J8.3 Hz, CH2P), 4.03(4 H, m, (CH3CH2O)2), 4.31(2H, t, J6.6 Hz, CH2ON), 6.60(2H, br.s, D2O exchangeable, NH2) 7.95(1H, s, H-8), 10.50(1H, br.s, D2O exchangeable, NH); Found C, 41.90; H, 5.94; N, 18.65%; C13H22N5O6P requires: C, 41.60; H, 5 91; N, 18.61%.

Workup

  1. customthen evaporated under reduced pressure
  2. customthen evaporated to dryness
  3. customPrecipitation from hot water

Sources & evidence

ORD record
ord-0c5c30eb8dc146cb9009bef186eaf0ae
Source dataset
uspto-grants-1991_10
Patent number
US05055458

Reaction notes

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