Trisodium Phosphate → HCID 135494296, compound

HRID 341913Notes

Reaction equation

HRID 341913 reaction equation
[NH2:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[C@@H:11]2[O:20][C@H:19]([CH2:21][OH:22])[C@@H:17]([OH:18])[C@H:12]2[O:13][CH2:14][CH2:15][CH3:16])=[C:4](N)[N:3]=1.NC1N=C2C(N=CN2[C@@H]2O[C@H](CO)[C@@H](OCCC)[C@H]2[OH:36])=C(N)N=1.[C@@H]1(N2C3N=CN=C(N)C=3N=C2)O[C@H](CO)[C@@H](O)[C@H]1O.P([O-])([O-])([O-])=O.[Na+].[Na+].[Na+]>P([O-])([O-])([O-])=O.CS(C)=O>[CH2:14]([O:13][C@@H:12]1[C@H:17]([OH:18])[C@@H:19]([CH2:21][OH:22])[O:20][C@H:11]1[N:8]1[C:9]2[N:10]=[C:2]([NH2:1])[NH:3][C:4](=[O:36])[C:5]=2[N:6]=[CH:7]1)[CH2:15][CH3:16]

Participants

7

Reactant 4

HCID 24243Trisodium PhosphateHCID 60961Adenosine2×HCID 10871038HCID 10871038, compoundHCID 11023772HCID 11023772, compound

Product 1

HCID 135494296HCID 135494296, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent2×HCID 1061PhosphateSolvent

Procedure

A mixture of 2,6-Diamino-9-(2'-O-propyl-β-D-ribofuranosyl) purine and 2,6-Diamino-9-(3'-O-propyl-β-D-ribofuranosyl) purine (4.6 gm) and adenosine deaminase (200 mg, Sigma Chemicals Type II) were stirred at room temperature overnight in 0.1M tris buffer (150 ml, pH 7.4), DMSO (100 ml) and 0.1M sodium phosphate buffer (10 ml). A further aliquot of adenosine deaminase (140 mg) in 0.1M phosphate buffer (30 ml) and DMSO (20 ml) was added and the reaction stirred an addition 24 hrs. The solvent was evaporated in vacuo and the residue flash chromatographed on silica gel utilizing 5→20% MeOH/CH2Cl2. Product-containing fractions were evaporated in vacuo and the residue crystallized from H2O to yield 2.6 gm of product. m.p. dec>270° C. 1H NMR (DMSO-d6) δ0.75 (t, 3, CH3), 1.42 (tq, 2, CH2), 3.3-3.6 (m, 4, H-5', O--CH2), 3,85 (m, 1), 4.2 (m, 1), 4.23 (m, 1), 5.10 (t, 1, 5'-OH), 5.13 (d, 1, 3'-OH), 5.75 (d, 1, H-1'), 6.45 (br s, 2, NH2), 7.95 (s, 1, H-8) and 10.67 (br s, 1, NH). Anal. Calcd. for C13H19N5O5 : C, 47.99; H, 5.89; N, 21.53. Found: C, 47.90, H, 5.85; N, 21.44.

Workup

  1. additionan addition 24 hrs
  2. customThe solvent was evaporated in vacuo
  3. customthe residue flash chromatographed on silica gel utilizing 5→20% MeOH/CH2Cl2
  4. customProduct-containing fractions were evaporated in vacuo
  5. customthe residue crystallized from H2O

Sources & evidence

ORD record
ord-590f3d701fe043cabf09550d7f304ecc
Source dataset
uspto-grants-1999_01
Patent number
US05856466

Reaction notes

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