Ammonia → 9-[2-(Diethoxyphosphorylmethoxy)ethoxy]adenine

HRID 6259Notes

Reaction equation

HRID 6259 reaction equation
Cl[C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[O:11][CH2:12][CH2:13][O:14][CH2:15][P:16]([O:21][CH2:22][CH3:23])([O:18][CH2:19][CH3:20])=[O:17].[NH3:24]>C(O)C>[CH2:19]([O:18][P:16]([CH2:15][O:14][CH2:13][CH2:12][O:11][N:6]1[CH:5]=[N:4][C:3]2[C:7]1=[N:8][CH:9]=[N:10][C:2]=2[NH2:24])([O:21][CH2:22][CH3:23])=[O:17])[CH3:20]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 148620656-Chloro-9-[2-(diethoxyphosphorylmethoxy)ethoxy]purine

Product 1

HCID 100431699-[2-(Diethoxyphosphorylmethoxy)ethoxy]adenine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 6-chloro-9-[2-(diethoxyphosphorylmethoxy)ethoxy]purine (1.45 g, 4 mmol) in ethanol (20 ml) saturated with ammonia gas was heated in a sealed steel vessel at 100° C. for 2 hours. The reaction mixture was cooled to ambient temperature, evaporated to dryness and the residual oil chromatographed on silica gel (eluted with dichloromethane: methanol, 90:10) to give recovered starting material (0.25 g) and the title compound (0.94 g, 82%--based on used starting material), crystallised from acetone-ether, m.p. 74°-76°. UV: λmax (EtOH) 260 nm (ε 13,500); IR: νmax (KBr) 3308, 3146, 1669, 1646, 1600, 1538, 1466, 1416, 1320, 1301, 1232, 1206, 1164, 1129. 1066, 1053, 1039, 1009, 978 cm-1 ; 1H NMR: δH [(CD3)2SO]1.24 (6H,t,J=7 Hz, (OCH2CH3)2), 3.83-3.89 (2H,m,CH2OCH2P), 3.91 (2H,d,J=8 Hz, OCH2P), 4.0-4.15 (4H, dq, J=7 Hz, 7 Hz, (OCH2CH3)2), 4.48-4.51 (2H,m,N-OCH2), 7.37 (2H,br.s,D2O exchangeable NH2), 8.14 (1H,s,H-8), 8.34 (1H,s,H-2). Found: C,41.74; H: 5.49; N: 20.06%; m/z 345.1202. C12H20N5O5P requires: C,41.74; H, 5.83; N, 20.28%; m/z 345.1212.

Workup

  1. customevaporated to dryness
  2. customthe residual oil chromatographed on silica gel (eluted with dichloromethane: methanol, 90:10)
  3. customto give
  4. customrecovered
  5. customthe title compound (0.94 g, 82%--based on used starting material), crystallised from acetone-ether, m.p. 74°-76°

Sources & evidence

ORD record
ord-a5113e4fda5d4aa09565a60ed377bd33
Source dataset
uspto-grants-1993_09
Patent number
US05247085

Reaction notes

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