Ammonia → HCID 136352429, compound

HRID 1017256Notes

Reaction equation

HRID 1017256 reaction equation
Br[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.[NH3:45]>CO.[Cu]>[NH2:45][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

5

Reactant 2

HCID 222AmmoniaHCID 136352428HCID 136352428, compound

Product 1

HCID 136352429HCID 136352429, compoundYield 36%

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 887MethanolSolvent

Procedure

3-Bromo-1-(2′,3′,5′-O-tribenzoyl-β-L-ribofdranosyl)pyrazolo[3,4-d]pyrimidin-4(5H)-one 24 (714 mg, 1.08 mmoles) was dissolved in MeOH saturated with NH3 at 0 C (30 mL). Thin copper wire (21 mg, 0.33 mmole) and cuprous chloride.(33 mg, 0.33 mmole) were added. The mixture in a sealed, stainless steel bomb was heated at 100 C for 16 h. After cooling, silica gel (2 g) was added to the reaction mixture and, the solvent evaporated. The silica gel absorbed with the crude product was loaded onto a silica column and eluted with 5% Et3N, 17% MeOH in CH2Cl2). The product was further purified by recrystallization (95% EtOH) to afford 3-amino-1-β-L-ribofuranosylpyrazolo[3,4-d]pyrirnidin-4(5H)-one 26 as a white needles (110 mg, 36%).

Workup

  1. addition(33 mg, 0.33 mmole) were added
  2. temperatureAfter cooling
  3. additionsilica gel (2 g) was added to the reaction mixture
  4. customthe solvent evaporated
  5. customThe silica gel absorbed with the crude product
  6. washeluted with 5% Et3N, 17% MeOH in CH2Cl2)
  7. customThe product was further purified by recrystallization (95% EtOH)

Sources & evidence

ORD record
ord-a930e3557e0e4578999aa172a21734b0
Source dataset
uspto-grants-2002_11
Patent number
US06479463B1

Reaction notes

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