HCID 19993538, compound → HCID 19993537, compound

HRID 345085Notes

Reaction equation

HRID 345085 reaction equation
[Si]([O:8][CH:9]([CH2:22][O:23][CH2:24][P:25]([O:30][CH2:31][CH3:32])([O:27][CH2:28][CH3:29])=[O:26])[CH2:10][O:11][N:12]1[CH:20]=[N:19][C:18]2[C:13]1=[N:14][CH:15]=[N:16][C:17]=2[NH2:21])(C(C)(C)C)(C)C>C(O)(=O)C>[CH2:28]([O:27][P:25]([CH2:24][O:23][CH2:22][CH:9]([OH:8])[CH2:10][O:11][N:12]1[CH:20]=[N:19][C:18]2[C:13]1=[N:14][CH:15]=[N:16][C:17]=2[NH2:21])([O:30][CH2:31][CH3:32])=[O:26])[CH3:29]

Participants

3

Reactant 1

HCID 19993538HCID 19993538, compound

Product 1

HCID 19993537HCID 19993537, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 9-[2-(t-butyldimethylsilyloxy)-3-(diethoxyphosphorylmethoxy)propoxy]adenine (410 mg, 0.84 mmol) in 80% acetic acid (20 ml) was stirred at 85° C. for 4 h. The solvents were evaporated in vacuo and the residue chromatographed on silica, eluting with chloroform-methanol 10:1, affording 9-[3-(diethoxyphosphorylmethoxy)-2-hydroxypropoxy]adenine (235 mg, 75%) as a white solid m.p. 84°-85° C. νmax (KBr) 3320, 1650, 1600 and 1460 cm-1 ; δH (CDCl3) 1.33 (6H, t, J6.8 Hz, 2×CH3CH2), 3.75 (2H, d, J5.5 Hz, CH2OCH2P), 3.87 (2H, d, J7.9 Hz, CH2P), 4.06 (1H, m, CHOH), 4.16 (4H, m, 2×CH3CH2), 4,42 (2H, m, CH2ON), 5.60 (1H, br.s, D2O exchangeable, OH), 5.84 (2H, br.s, D2O exchangeable, NH2), 8.01 (1H, s, H-2/H-8), 8.35 (1H, s, H-2/H-8). Found: C, 41.66; H, 5.95; N, 18.55%; M+ 375.1306.C13H22N5O6P requires C, 41.60; H, 5.91; N, 18.66%; M+ 375.1308.

Workup

  1. customThe solvents were evaporated in vacuo
  2. customthe residue chromatographed on silica
  3. washeluting with chloroform-methanol 10:1

Sources & evidence

ORD record
ord-6feacdcd18b3438fb11c688c215352bf
Source dataset
uspto-grants-1991_10
Patent number
US05055458

Reaction notes

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