Ammonia → HCID 10839443, compound

HRID 1369955Notes

Reaction equation

HRID 1369955 reaction equation
Cl[C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[C@@H:11]1[O:24][C@H:23]([CH2:25][O:26][C:27]([C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C@@H:13]([O:14]C(=O)C2C=CC=CC=2)[C@@H:12]1[F:46].[NH3:47]>>[C:27]([O:26][CH2:25][C@H:23]1[O:24][C@@H:11]([N:6]2[CH:5]=[N:4][C:3]3[C:7]2=[N:8][CH:9]=[N:10][C:2]=3[NH2:47])[C@@H:12]([F:46])[C@@H:13]1[OH:14])([C:40]1[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=1)([C:34]1[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=1)[C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1

Participants

3

Reactant 2

HCID 222AmmoniaHCID 10841755HCID 10841755, compound

Product 1

HCID 10839443HCID 10839443, compoundYield 73%

Procedure

6-Chloro-9-(5-O-trityl-3-O-benzoyl-2-deoxy-2-fluoro-β-D-arabinofuranosyl)-9-H-purine (3.15 g, 4.98 mmol) was dissolved in 100 ml methanolic ammonia (saturated at 0° C.) and left in a sealed tube at 100° C. for 2 days. After cooling, the solvent was carefully distilled off, and the residues were dissolved in 100 ml chloroform. The insolubles were filtered off and the solution was applied to a silica gel column (3.5×50 cm) and eluted with 3 to 10% ethanol/methylene chloride solution (4000 ml). Product fractions were collected, and the solution was concentrated to give white crystals (1.87 g, 3.66 mmol, 73%)

Workup

  1. temperatureAfter cooling
  2. distillationthe solvent was carefully distilled off
  3. dissolutionthe residues were dissolved in 100 ml chloroform
  4. filtrationThe insolubles were filtered off
  5. washeluted with 3 to 10% ethanol/methylene chloride solution (4000 ml)
  6. customProduct fractions were collected
  7. concentrationthe solution was concentrated

Sources & evidence

ORD record
ord-1456ecd93c654e7d9b114786a3830ef6
Source dataset
uspto-grants-2003_06
Patent number
US06579976B2

Reaction notes

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