((1S,2R,3S,4R)-4-{6-(2,2-diphenyl-ethylamino)-2-[(R)-3-(3-pyridin-3-yl-ureido)-pyrrolidin-1-yl]-purin-9-yl}-2,3-dihydroxy-cyclopentyl)-carbamic acid benzyl ester trifluoroacetate → 1-{(R)-1-[9-((1R,2S,3R,4S)-4-amino-2,3-dihydroxy-cyclopentyl)-6-(2,2-diphenyl-ethylamino)-9H-purin-2-yl]-pyrrolidin-3-yl}-3-pyridin-3-yl-urea

HRID 1882591Notes

Reaction equation

HRID 1882591 reaction equation
FC(F)(F)C(O)=O.C(OC(=O)[NH:17][C@H:18]1[CH2:22][C@@H:21]([N:23]2[CH:31]=[N:30][C:29]3[C:24]2=[N:25][C:26]([N:47]2[CH2:51][CH2:50][C@@H:49]([NH:52][C:53]([NH:55][C:56]4[CH:57]=[N:58][CH:59]=[CH:60][CH:61]=4)=[O:54])[CH2:48]2)=[N:27][C:28]=3[NH:32][CH2:33][CH:34]([C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[C@H:20]([OH:62])[C@@H:19]1[OH:63])C1C=CC=CC=1>C(O)C.[Pd]>[NH2:17][C@H:18]1[CH2:22][C@@H:21]([N:23]2[CH:31]=[N:30][C:29]3[C:24]2=[N:25][C:26]([N:47]2[CH2:51][CH2:50][C@@H:49]([NH:52][C:53]([NH:55][C:56]4[CH:57]=[N:58][CH:59]=[CH:60][CH:61]=4)=[O:54])[CH2:48]2)=[N:27][C:28]=3[NH:32][CH2:33][CH:34]([C:35]2[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=2)[C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[C@H:20]([OH:62])[C@@H:19]1[OH:63]

Participants

4

Reactant 1

HCID 66631160((1S,2R,3S,4R)-4-{6-(2,2-diphenyl-ethylamino)-2-[(R)-3-(3-pyridin-3-yl-ureido)-pyrrolidin-1-yl]-purin-9-yl}-2,3-dihydroxy-cyclopentyl)-carbamic acid benzyl ester trifluoroacetate

Product 1

HCID 666296911-{(R)-1-[9-((1R,2S,3R,4S)-4-amino-2,3-dihydroxy-cyclopentyl)-6-(2,2-diphenyl-ethylamino)-9H-purin-2-yl]-pyrrolidin-3-yl}-3-pyridin-3-yl-urea

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of ((1S,2R,3S,4R)-4-{6-(2,2-diphenyl-ethylamino)-2-[(R)-3-(3-pyridin-3-yl-ureido)-pyrrolidin-1-yl]-purin-9-yl}-2,3-dihydroxy-cyclopentyl)-carbamic acid benzyl ester trifluoroacetate (35 mg, 46 μmol) in ethanol (1 ml) under an inert atmosphere of Argon is added 10% palladium on carbon (10 mg). The reaction mixture is purged with Argon and placed under a positive atmosphere of hydrogen overnight after which time, the mixture is filtered through celite and the catalyst washed with ethanol. The organic portions are combined and concentrated in vacuo to yield the title compound. MS (ES+) m/e 635 (MH+).

Workup

  1. customThe reaction mixture is purged with Argon
  2. customplaced under a positive atmosphere of hydrogen overnight
  3. filtrationthe mixture is filtered through celite
  4. washthe catalyst washed with ethanol
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8e198d56af5b455683e9f0d79c5fed3f
Source dataset
uspto-grants-2012_11
Patent number
US08318750B2

Reaction notes

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