Triphenylphosphine → (2S,4S)-tert-butyl 2-((tert-butyldiphenylsilyloxy)methyl)-4-(4-chloro-5-iodo-7H-pyrrolo[2,3-d]pyrimidin-7-yl)pyrrolidine-1-carboxylate

HRID 516173Notes

Reaction equation

HRID 516173 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C.[Cl:34][C:35]1[C:36]2[C:43]([I:44])=[CH:42][NH:41][C:37]=2[N:38]=[CH:39][N:40]=1.[Si:45]([O:62][CH2:63][C@@H:64]1[CH2:68][C@@H:67](O)[CH2:66][N:65]1[C:70]([O:72][C:73]([CH3:76])([CH3:75])[CH3:74])=[O:71])([C:58]([CH3:61])([CH3:60])[CH3:59])([C:52]1[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=1)[C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1>C1COCC1.O.C(OCC)(=O)C>[Si:45]([O:62][CH2:63][C@@H:64]1[CH2:68][C@H:67]([N:41]2[C:37]3[N:38]=[CH:39][N:40]=[C:35]([Cl:34])[C:36]=3[C:43]([I:44])=[CH:42]2)[CH2:66][N:65]1[C:70]([O:72][C:73]([CH3:76])([CH3:75])[CH3:74])=[O:71])([C:58]([CH3:60])([CH3:61])[CH3:59])([C:52]1[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=1)[C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1

Participants

8

Reactant 4

HCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 148092816-Chloro-7-iodo-7-deazapurineHCID 69332404HCID 69332404, compound

Product 1

HCID 89870881(2S,4S)-tert-butyl 2-((tert-butyldiphenylsilyloxy)methyl)-4-(4-chloro-5-iodo-7H-pyrrolo[2,3-d]pyrimidin-7-yl)pyrrolidine-1-carboxylate

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

A solution of triphenylphosphine (443 mg) in THF (25 ml) was cooled to 0° C., and DIAD (340 μl) was added thereto dropwise. The reaction mixture was stirred at 0° C. for 1 hour. 4-Chloro-5-iodo-7H-pyrrolo[2,3-d]pyrimidine (363 mg) and the (2S,4R)-tert-butyl 2-((tert-butyldiphenylsilyloxy)methyl)-4-hydroxypyrrolidine-1-carboxylate (651.6 mg) obtained in Example 28 (Step 1) were added thereto, and stirred at room temperature overnight. Ethyl acetate and water were added to separate the organic layer. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The resulting residue was purified by silica gel column chromatography (developing solvent: hexane/ethyl acetate) to obtain the title compound as a light-yellow, amorphous substance (400 mg). m/z [M+H]+ 718.5

Workup

  1. stirringstirred at room temperature overnight
  2. customto separate the organic layer
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe resulting residue was purified by silica gel column chromatography (developing solvent: hexane/ethyl acetate)

Sources & evidence

ORD record
ord-5cbee11f616e4b389d2b3731120db7a7
Source dataset
uspto-grants-2015_08
Patent number
US09108973B2

Reaction notes

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