2-Amino-7-[3,5-bis-o-(2,4-dichlorophenylmethyl)-2-c,2-o-dimethyl-beta-d-ribofuranosyl]-5-methyl-7h-pyrrolo[2,3-d]pyrimidine-4(3h)-one → 2-Amino-5-methyl-7-(5-o-benzyl-2-c,2-o-dimethyl-beta-d-ribofuranosyl)-7h-pyrrolo[2,3-d]pyrimidin-4(3h)-one

HRID 2212926Notes

Reaction equation

HRID 2212926 reaction equation
[NH2:1][C:2]1[NH:3][C:4](=[O:41])[C:5]2[C:10]([CH3:11])=[CH:9][N:8]([C@@H:12]3[O:28][C@H:27]([CH2:29][O:30][CH2:31][C:32]4[CH:37]=[CH:36][C:35](Cl)=[CH:34][C:33]=4Cl)[C@@H:16]([O:17]CC4C=CC(Cl)=CC=4Cl)[C@@:13]3([CH3:40])[O:14][CH3:15])[C:6]=2[N:7]=1>CO.CCN(CC)CC.[Pd]>[NH2:1][C:2]1[NH:3][C:4](=[O:41])[C:5]2[C:10]([CH3:11])=[CH:9][N:8]([C@@H:12]3[O:28][C@H:27]([CH2:29][O:30][CH2:31][C:32]4[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=4)[C@@H:16]([OH:17])[C@@:13]3([CH3:40])[O:14][CH3:15])[C:6]=2[N:7]=1

Participants

5

Reactant 1

HCID 1363907652-Amino-7-[3,5-bis-o-(2,4-dichlorophenylmethyl)-2-c,2-o-dimethyl-beta-d-ribofuranosyl]-5-methyl-7h-pyrrolo[2,3-d]pyrimidine-4(3h)-one

Product 1

HCID 1363907662-Amino-5-methyl-7-(5-o-benzyl-2-c,2-o-dimethyl-beta-d-ribofuranosyl)-7h-pyrrolo[2,3-d]pyrimidin-4(3h)-one

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8471TriethylamineSolvent

Procedure

A mixture of the product from Step C (64 mg, 0.1 mmol) in MeOH (5 mL) and Et3N (0.2 mL) and 10% Pd/C (24 mg) was hydrogenated on a Parr hydrogenator at 50 psi at r.t. for 1.5 days, then filtered through a Celite pad which was thoroughly washed with MeOH. The combined filtrate was evaporated and the residue purified on a silica gel column (3×4 cm) with CH2Cl2/MeOH (30/1, 20/1) as eluent to yield 2-amino-5-methyl-7-(5-O-benzyl-2-C,2-O-dimethyl-β-D-ribofuranosyl)-7H-pyrrolo[2,3-d]pyrimidin-4(3H)-one. The compound (37 mg) was further hydrogenated in EtOH (2 mL) with 10% Pd/C and under atmospheric pressure of hydrogen. After stirring 2 days at r.t., the reaction mixture was filtered through Celite, the filtrate evaporated and the crude product purified on a silica gel column (1×7 cm) with CH2Cl2/MeOH (30/1, 20/1 and 10/1) as eluent to yield the title compound (12 mg) after freeze-drying.

Workup

  1. filtrationfiltered through a Celite pad which
  2. washwas thoroughly washed with MeOH
  3. customThe combined filtrate was evaporated
  4. customthe residue purified on a silica gel column (3×4 cm) with CH2Cl2/MeOH (30/1, 20/1) as eluent

Sources & evidence

ORD record
ord-4a5d67559d4e43d9ac9694ae16265ebb
Source dataset
uspto-grants-2006_09
Patent number
US07105499B2

Reaction notes

Loading…