HCID 136352428, compound → HCID 136352427, compound

HRID 1017255Notes

Reaction equation

HRID 1017255 reaction equation
[Br:1][C:2]1[C:10]2[C:9](=[O:11])[NH:8][CH:7]=[N:6][C:5]=2[N:4]([C@H:12]2[O:18][C@@H:17]([CH2:19][O:20]C(=O)C3C=CC=CC=3)[C@:15](C(=O)C3C=CC=CC=3)([OH:16])[C@:13]2(C(=O)C2C=CC=CC=2)[OH:14])[N:3]=1>CO.N>[Br:1][C:2]1[C:10]2[C:9](=[O:11])[NH:8][CH:7]=[N:6][C:5]=2[N:4]([C@H:12]2[O:18][C@@H:17]([CH2:19][OH:20])[C@H:15]([OH:16])[C@@H:13]2[OH:14])[N:3]=1

Participants

4

Reactant 1

HCID 136352428HCID 136352428, compound

Product 1

HCID 136352427HCID 136352427, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 222AmmoniaSolventHCID 887MethanolSolvent

Procedure

3-Bromo-1-(2′,3′,5′-O-tribenzoy-β-L-ribofuranosyl)pyrazolo[3,4-d]pyrimidin-4(5H)-one 24 (280 mg, 0.43 mmole) was dissolved in MeOH saturated with NH3 at 0 C (25 mL). The solution in a sealed, stainless steel bomb was heated at 100 C for 6 h. After cooling, ammonia and methanol were evaporated. The residue was dissolved in water (40 mL), washed with EtOAc (4×20 mL), and concentrated. The residue was soaked in acetonitrile and the resulting solid filtered, dried under vacuum to give 3-Bromo-1-β-L-ribofuranosylpyrazolo[3,4-d]pyrimidin-4(5H)-one 25 as a white solid (140 mg, 95%).

Workup

  1. temperatureAfter cooling
  2. customammonia and methanol were evaporated
  3. dissolutionThe residue was dissolved in water (40 mL)
  4. washwashed with EtOAc (4×20 mL)
  5. concentrationconcentrated
  6. filtrationthe resulting solid filtered
  7. customdried under vacuum

Sources & evidence

ORD record
ord-88ce521518df4c329bd7c8b3f0b77dd6
Source dataset
uspto-grants-2002_11
Patent number
US06479463B1

Reaction notes

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