7-Amino-1-(2,3,5-tri-O-benzoyl-beta-D-ribofuranosyl)-1,3-aza-phospholo[4,5-d]pyrimidine → 7-Amino-1-(beta-D-ribofuranosyl)-1,3-azaphospholo-[4,5-d]pyrimidine

HRID 1108787Notes

Reaction equation

HRID 1108787 reaction equation
[NH2:1][C:2]1[C:3]2[N:10]([C@@H:11]3[O:33][C@H:32]([CH2:34][O:35]C(=O)C4C=CC=CC=4)[C@@H:22]([O:23]C(=O)C4C=CC=CC=4)[C@H:12]3[O:13]C(=O)C3C=CC=CC=3)[CH:9]=[P:8][C:4]=2[N:5]=[CH:6][N:7]=1>N>[NH2:1][C:2]1[C:3]2[N:10]([C@@H:11]3[O:33][C@H:32]([CH2:34][OH:35])[C@@H:22]([OH:23])[C@H:12]3[OH:13])[CH:9]=[P:8][C:4]=2[N:5]=[CH:6][N:7]=1

Participants

3

Reactant 1

HCID 219688567-Amino-1-(2,3,5-tri-O-benzoyl-beta-D-ribofuranosyl)-1,3-aza-phospholo[4,5-d]pyrimidine2×

Product 1

HCID 97957957-Amino-1-(beta-D-ribofuranosyl)-1,3-azaphospholo-[4,5-d]pyrimidineYield 84.4%

Reagents, catalysts & solvents 1

HCID 222AmmoniaSolvent

Procedure

A mixture of 7-Amino-1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-1,3-azaphospholo[4,5-d]pyrimidine (compound 21 , R=2,3,5-tri-O-benzoyl-β-ribofuranose, 0.45 g, 0.75 mmol) and methanolic ammonia (100 mL, saturated at 0° C.) was stirred at room temperature for 20 h and the methanolic ammonia was evaporated under reduced pressure. The residue was triturated with methanol (10 mL) and the product was collected by filtration. The filtrate was evaporated and the residue was purified by chromatography over a silica gel column. The column was flash eluted with dichloromethane containing 0-20% methanol. The appropriate fractions containing the pure product were collected and evaporated to give a total yield of 0.18 g (84%) of the title compound, mp 220-222° C. Ir (KBr): ν700 (=P-C), 1205 (-P=CH), and 2930-3470 (NH2, OH) cm-1. Uv (pH 1): λmax254 nm (ε23,400), 284 (15,600), and 314 (5600); (MeOH): λmax266 nm (ε32,900), and 340 (2100); (pH 11): 266 nm (ε36,050), and 338 (3250). 31 p nmr (DMSO-d6): δ 62.50; 1H nmr (DMSO-d6): δ3.73(dd,2H, C5'H2), 3.98 (m, 1 H, C4'H), 4.10 (br s, 1 H, C3'H), 4.28 (m, 1 H, C2'H), 5.24 (br s, 2 H, 2OH), 5.63 (br s, 1 H, OH), 5.70 (d, 1 H, C1'H), 8.24 (s, 2 H, NH2), 8.86 (d, 1 H, C5H), and 8.83 (d, 1 H, J =58.8 Hz, C2H). Anal. Calcd. for C10H13N4O4P.0.25 CH2Cl2 :C, 40.30; H, 4.45; N, 18.35. Found: C, 40.40; H, 4.15; N, 18.54.

Workup

  1. customthe methanolic ammonia was evaporated under reduced pressure
  2. customThe residue was triturated with methanol (10 mL)
  3. filtrationthe product was collected by filtration
  4. customThe filtrate was evaporated
  5. customthe residue was purified by chromatography over a silica gel column
  6. washeluted with dichloromethane containing 0-20% methanol
  7. additionThe appropriate fractions containing the pure product
  8. customwere collected
  9. customevaporated

Sources & evidence

ORD record
ord-e966720bdbf145f4a6841ee5aeb6e17c
Source dataset
uspto-grants-2000_05
Patent number
US06069132

Reaction notes

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