HCID 86609570, compound → HCID 68853337, compound

HRID 2108347Notes

Reaction equation

HRID 2108347 reaction equation
[OH:1][C@H:2]1[C@@H:6]([OH:7])[C@H:5]([CH2:8][OH:9])[O:4][C@H:3]1[N:10]1[CH:18]=[N:17][C:16]2[C:11]1=[N:12][C:13]([N:25]1[CH:29]=[C:28](/[CH:30]=[CH:31]/[C:32]([O:34][CH2:35][CH3:36])=[O:33])[CH:27]=[N:26]1)=[N:14][C:15]=2[NH:19][CH:20]1[CH2:24][CH2:23][CH2:22][CH2:21]1>[Pd].CO>[OH:1][C@H:2]1[C@@H:6]([OH:7])[C@H:5]([CH2:8][OH:9])[O:4][C@H:3]1[N:10]1[CH:18]=[N:17][C:16]2[C:11]1=[N:12][C:13]([N:25]1[CH:29]=[C:28]([CH2:30][CH2:31][C:32]([O:34][CH2:35][CH3:36])=[O:33])[CH:27]=[N:26]1)=[N:14][C:15]=2[NH:19][CH:20]1[CH2:24][CH2:23][CH2:22][CH2:21]1

Participants

4

Reactant 1

HCID 86609570HCID 86609570, compound

Product 1

HCID 68853337HCID 68853337, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

10 mg of the ethyl (2E)-3-(1-{9-[(3S,5S,2R,4R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-6-(cyclopentylamino)purin-2-yl}pyrazol-4-yl)prop-2-enoate prepared in the preceding step was combined in a par bottle with 3 mL of MeOH and approximately 5 mg of 10% Pd/C (Aldrich) and the solution hydrogenated at 25-30 psi at room temperature. The Pd/c was filtered off and the filtrate condensed to provide ethyl 3-(1-{9-[(3S,5S,2R,4R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-6-(cyclopentylamino)purin-2-yl}pyrazol-4-yl)propanoate.

Workup

  1. customhydrogenated at 25-30 psi at room temperature
  2. filtrationThe Pd/c was filtered off
  3. customthe filtrate condensed

Sources & evidence

ORD record
ord-94dcef7d67e9486e8f58f9b2eb38a04d
Source dataset
uspto-grants-2009_04
Patent number
US07514417B2

Reaction notes

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