(2R,3R,4R,5R)-2-(2-amino-4-chloropyrrolo[2,3-d]pyrimidin-7-yl)-5-(hydroxymethyl)-3-methyloxolane-3,4-diol → 7-(2-C-Methyl-b-D-ribofuranosyl)-7H-pyrrolo[2,3-d]pyrimidin-2-amine

HRID 2212922Notes

Reaction equation

HRID 2212922 reaction equation
[NH2:1][C:2]1[N:3]=[C:4](Cl)[C:5]2[CH:10]=[CH:9][N:8]([C@@H:11]3[O:17][C@H:16]([CH2:18][OH:19])[C@@H:14]([OH:15])[C@@:12]3([CH3:20])[OH:13])[C:6]=2[N:7]=1>CCO.N1C=CC=CC=1.[Pd]>[NH2:1][C:2]1[N:3]=[CH:4][C:5]2[CH:10]=[CH:9][N:8]([C@@H:11]3[O:17][C@H:16]([CH2:18][OH:19])[C@@H:14]([OH:15])[C@@:12]3([CH3:20])[OH:13])[C:6]=2[N:7]=1

Participants

5

Reactant 1

HCID 11483860(2R,3R,4R,5R)-2-(2-amino-4-chloropyrrolo[2,3-d]pyrimidin-7-yl)-5-(hydroxymethyl)-3-methyloxolane-3,4-diol

Product 1

HCID 98788017-(2-C-Methyl-b-D-ribofuranosyl)-7H-pyrrolo[2,3-d]pyrimidin-2-amineYield 81.6%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 1049PyridineSolvent

Procedure

A mixture of 2-amino-4-chloro-7-(2-C-methyl-β-D-ribofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine (Example 118, Step B) (20 mg, 0.07 mmol) in EtOH (1.0 mL), pyridine (0.1 mL) and 10% Pd/C (6 mg) under H2 (atmospheric pressure) was stirred overnight at room temperature. The mixture was filtered through a Celite pad which was thoroughly washed with EtOH. The combined filtrate was evaporated and purified on a silica gel column with CH2Cl2/MeOH, 20/1 and 10/1, as eluent to give the title compound as a white solid (16 mg).

Workup

  1. filtrationThe mixture was filtered through a Celite pad which
  2. washwas thoroughly washed with EtOH
  3. customThe combined filtrate was evaporated
  4. custompurified on a silica gel column with CH2Cl2/MeOH, 20/1 and 10/1, as eluent

Sources & evidence

ORD record
ord-3008abdb90454282acf35e351777e7e5
Source dataset
uspto-grants-2006_09
Patent number
US07105499B2

Reaction notes

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