Triphenylphosphine → HCID 18647638, compound

HRID 128571Notes

Reaction equation

HRID 128571 reaction equation
[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([NH:6][CH:7]=[N:8]2)=[C:4]([Cl:11])[N:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O.[O:43]([C@:51]([C@@H:59]([CH:61]([O:63][Si:64]([C:67]([CH3:70])([CH3:69])[CH3:68])([CH3:66])[CH3:65])[OH:62])[OH:60])([OH:58])[C:52]([F:57])([F:56])[C:53](O)=[O:54])[Si:44]([C:47]([CH3:50])([CH3:49])[CH3:48])([CH3:46])[CH3:45]>O1CCCC1>[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[C:53]([C:52]([F:57])([F:56])[C@@:51]([O:43][Si:44]([C:47]([CH3:50])([CH3:49])[CH3:48])([CH3:46])[CH3:45])([C@@H:59]([CH:61]([O:63][Si:64]([C:67]([CH3:70])([CH3:69])[CH3:68])([CH3:66])[CH3:65])[OH:62])[OH:60])[OH:58])=[O:54])=[C:4]([Cl:11])[N:3]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 53244122,6-DichloropurineHCID 18647641HCID 18647641, compound

Product 1

HCID 18647638HCID 18647638, compoundYield 40.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 1.89 g (10.0 mmol) of 2,6-dichloropurine in 100 ml of tetrahydrofuran was added 2.62 g (10.0 mmol) of triphenylphosphine and 1.74 g (10.0 mmol) of diethyl azodicarboxylate. To this mixture was added a solution of 3.98 g (10.0 mmol) of 3,5-bis(t-butyldimethylsiloxy)-1-hydroxy-2-desoxy-2,2-difluororibose in 25 ml of tetrahydrofuran and the mixture was stirred at room temperature overnight. The precipitated solid was removed by vacuum filtration and the filtrate was concentrated under vacuum. The residue was dissolved in 100 ml of diethyl ether and the solution was stirred at room temperature overnight. The mixture was filtered and the filtrate was evaporated to dryness under vacuum. The residue was dissolved in 25 ml of ethyl acetate, and the mixture was set in the refrigerator. The mixture was filtered and the filtrate was chromatographed by HPLC while eluting with hexane/ethyl acetate (4/1, v/v). The first chromaphore containing fractions were combined and the solvent was evaporated therefrom to provide 2.5 g of 1-(2,6-dichloro-9H-purin-9-yl)-3,5-bis(t-butyldimethylsiloxy)-2-desoxy-2,2-difluororibose. m/e=[568-(t-butyl)]=511

Workup

  1. customThe precipitated solid was removed by vacuum filtration
  2. concentrationthe filtrate was concentrated under vacuum
  3. dissolutionThe residue was dissolved in 100 ml of diethyl ether
  4. stirringthe solution was stirred at room temperature overnight
  5. filtrationThe mixture was filtered
  6. customthe filtrate was evaporated to dryness under vacuum
  7. dissolutionThe residue was dissolved in 25 ml of ethyl acetate
  8. filtrationThe mixture was filtered
  9. customthe filtrate was chromatographed by HPLC
  10. washwhile eluting with hexane/ethyl acetate (4/1
  11. additionThe first chromaphore containing fractions
  12. customthe solvent was evaporated

Sources & evidence

ORD record
ord-99f85928288e42189579b3660cbc3305
Source dataset
uspto-grants-1995_11
Patent number
US05464826

Reaction notes

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