4-Amino-7-[3,5-bis-o-(2,4-dichlorophenylmethyl)-2-c-hydroxymethyl-beta-d-ribofuranosyl]-7h-pyrrolo[2,3-d]pyrimidine → 4-Amino-7-(2-C-hydroxymethyl-beta-D-ribofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine

HRID 2212935Notes

Reaction equation

HRID 2212935 reaction equation
[NH2:1][C:2]1[C:3]2[CH:10]=[CH:9][N:8]([C@@H:11]3[O:26][C@H:25]([CH2:27][O:28]CC4C=CC(Cl)=CC=4Cl)[C@@H:14]([O:15]CC4C=CC(Cl)=CC=4Cl)[C@@:12]3([CH2:38][OH:39])[OH:13])[C:4]=2[N:5]=[CH:6][N:7]=1>CO.ClCCl.[Pd]>[NH2:1][C:2]1[C:3]2[CH:10]=[CH:9][N:8]([C@@H:11]3[O:26][C@H:25]([CH2:27][OH:28])[C@@H:14]([OH:15])[C@@:12]3([CH2:38][OH:39])[OH:13])[C:4]=2[N:5]=[CH:6][N:7]=1

Participants

4

Reactant 1

HCID 671429394-Amino-7-[3,5-bis-o-(2,4-dichlorophenylmethyl)-2-c-hydroxymethyl-beta-d-ribofuranosyl]-7h-pyrrolo[2,3-d]pyrimidine

Product 1

HCID 99659694-Amino-7-(2-C-hydroxymethyl-beta-D-ribofuranosyl)-7H-pyrrolo[2,3-d]pyrimidineYield 84.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumSolventHCID 21226129Dichloromethane methanolSolvent

Procedure

The compound from Step B (120 mg, 0.2 mmol) was dissolved in 1:1 methanol/dichloromethane, 10% Pd-C was added, and the suspension stirred under an H2 atmosphere for 12 h. The catalyst was removed by filtration through a celite pad and washed with copious amounts of methanol. The combined filtrate was evaporated in vacuo and the residue was purified by flash chromatography (SiO2, 10% methanol in EtOAc containing 0.1% triethylamine) to give the title compound (50 mg) as a white powder.

Workup

  1. additionwas added
  2. customThe catalyst was removed by filtration through a celite pad
  3. washwashed with copious amounts of methanol
  4. customThe combined filtrate was evaporated in vacuo
  5. customthe residue was purified by flash chromatography (SiO2, 10% methanol in EtOAc containing 0.1% triethylamine)

Sources & evidence

ORD record
ord-7cdd608bf60941aa9fdee6cdcd0225b4
Source dataset
uspto-grants-2006_09
Patent number
US07105499B2

Reaction notes

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