Triphenylphosphine → HCID 3011897, compound

HRID 2252711Notes

Reaction equation

HRID 2252711 reaction equation
[F:1][C:2]1[C:10]2[C:9](Cl)=[N:8][CH:7]=[N:6][C:5]=2[NH:4][CH:3]=1.C([O:20][C@:21]1([CH3:46])[C@H:26]([O:27]C(=O)C2C=CC=CC=2)[C@@H:25]([CH2:36][O:37]C(=O)C2C=CC=CC=2)[O:24][CH:22]1O)(=O)C1C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[N:66](C(OCC)=O)=NC(OCC)=O>C1COCC1>[NH2:66][C:9]1[C:10]2[C:2]([F:1])=[CH:3][N:4]([C@@H:22]3[O:24][C@H:25]([CH2:36][OH:37])[C@@H:26]([OH:27])[C@@:21]3([CH3:46])[OH:20])[C:5]=2[N:6]=[CH:7][N:8]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 113212244-Chloro-5-fluoro-7H-pyrrolo(2,3-d)pyrimidineHCID 573769702,3,5-Tri-O-benzoyl-2-C-methyl-D-ribofuranose

Product 1

HCID 3011897HCID 3011897, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the compound from Step C (0.075 g, 0.44 mmol), 2,3,5-tri-O-benzoyl-2-C-methyl-D-ribofuranose [Harry-O'kuru, Rogers E.; Smith, Jennifer M.; Wolfe, Michael S, “A Short, Flexible Route toward 2′-C-Branched Ribonucleosides,” J. Org. Chem., 62: 1754-1759 (1997)] (4-5) (0.25 g, 0.53 mmol) and triphenylphosphine (0.23 g, 0.88 mmol) in THF (15 mL) was added diethyl azodicarboxylate (DEAD) (0.14 mL, 0.88 mmol). The reaction mixture was stirred at room temperature overnight. The solution was directly adsorbed onto silica gel and purified over silica gel using ethyl acetate/hexane 1:9 as the eluent Appropriate fractions were dissolved in dioxane (3 mL) and liquid ammonia (4 mL) and the mixture was heated in a steel bomb at 85° C. for 24 h. The solvent was evaporated and the residue was purified over silica gel using methanol/dichloromethane (1:9) as the eluent. Fractions containing the desired compound were pooled and evaporated in vacuo to give the title compound.

Workup

  1. custompurified over silica gel
  2. dissolutionwere dissolved in dioxane (3 mL)
  3. temperatureliquid ammonia (4 mL) and the mixture was heated in a steel bomb at 85° C. for 24 h
  4. customThe solvent was evaporated
  5. customthe residue was purified over silica gel
  6. additionFractions containing the desired compound
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-4e5d69bbec084ad8a5c87d62bb126d20
Source dataset
uspto-grants-2008_01
Patent number
US07323453B2

Reaction notes

Loading…