HCID 67150793, compound → HCID 11260911, compound

HRID 549776Notes

Reaction equation

HRID 549776 reaction equation
C([O:8][C:9]1[C:10]([O:15][CH2:16][CH:17]2[CH:21]3[O:22][C:23]([CH3:26])([CH3:25])[O:24][CH:20]3[CH:19]([N:27]3[CH:35]=[N:34][C:33]4[C:28]3=[N:29][CH:30]=[N:31][C:32]=4[NH:36][C:37]([NH:39][C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=3)=[O:38])[O:18]2)=[N:11][CH:12]=[CH:13][CH:14]=1)C1C=CC=CC=1>CO.C(OCC)(=O)C.[Pd]>[OH:8][C:9]1[C:10]([O:15][CH2:16][CH:17]2[CH:21]3[O:22][C:23]([CH3:26])([CH3:25])[O:24][CH:20]3[CH:19]([N:27]3[CH:35]=[N:34][C:33]4[C:28]3=[N:29][CH:30]=[N:31][C:32]=4[NH:36][C:37]([NH:39][C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=3)=[O:38])[O:18]2)=[N:11][CH:12]=[CH:13][CH:14]=1

Participants

4

Reactant 1

HCID 67150793HCID 67150793, compound

Product 1

HCID 11260911HCID 11260911, compoundYield 32.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21584119Ethylacetate methanolSolvent

Procedure

Dry argon was bubbled through a solution of 1-{9-[6-(3-Benzyloxy-pyridin-2-yloxymethyl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-9H-purin-6-yl}-3-phenyl-urea (18 mg, 0.03 mmol, prepared as above) in methanol/ethyl acetate (1:1 v/v, 10 mL) at 23° C. for 10 min. Palladium on activated carbon (10%) was added and the suspension was degassed by argon for another 5 min. Hydrogen (H2) was conducted to the solution via a balloon, and the reaction proceeded for 5 h. The mixture was filtered and concentrated in vacuo to give the crude product. Preparative reverse-phase HPLC was used to obtain the pure compound (5 mg, 31% yield) as a white solid. MW calculated for C25H25N7O6 (MH+) 520. found 520 by LCMS.

Workup

  1. customthe suspension was degassed by argon for another 5 min
  2. filtrationThe mixture was filtered
  3. concentrationconcentrated in vacuo
  4. customto give the crude product

Sources & evidence

ORD record
ord-f3f655d657d041c19f266c37cdae9c8e
Source dataset
uspto-grants-2011_05
Patent number
US07943760B2

Reaction notes

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