Triphenylphosphine → 2'-Amino-2'-deoxy-5-iodouridine

HRID 618963Notes

Reaction equation

HRID 618963 reaction equation
[I:1][C:2]1[C:3](=[O:20])[NH:4][C:5](=[O:19])[N:6]([CH:18]=1)[C@@H:7]1[O:14][C@H:11]([CH2:12][OH:13])[C@@H:9]([OH:10])[C@H:8]1[N:15]=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCOCC1>[I:1][C:2]1[C:3](=[O:20])[NH:4][C:5](=[O:19])[N:6]([CH:18]=1)[C@@H:7]1[O:14][C@H:11]([CH2:12][OH:13])[C@@H:9]([OH:10])[C@H:8]1[NH2:15]

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 867511782'-Azido-2'-deoxy-5-iodouridine

Product 1

HCID 694591682'-Amino-2'-deoxy-5-iodouridineYield 78%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 5-iodo,2'-azido,2'-deoxyuridine (2.48 g, 6.3 mmoles) in dioxane (33 ml) is added triphenylphosphine (5.8 g, 22 mmoles, 3.5 eq.) and the mixture is stirred at room temperature for 1 h, during which time a white precipitate forms. The precipitate is collected and washed three times with diethyl ether (3×50 ml). The filtrate is evaporated to dryness, taken up in a minimum amount of dioxane, and stored at -20° C. for 48 h. The precipitate is collected and washed with diethyl ether. The combined precipitates gave 1.81 g of 5-iodo,2'-amino,2'-deoxyuridine (78% yield). The spectral properties agreed with those reported in the literature (Verheyden et al. (1971) supra).

Workup

  1. customThe precipitate is collected
  2. washwashed three times with diethyl ether (3×50 ml)
  3. customThe filtrate is evaporated to dryness
  4. waitstored at -20° C. for 48 h
  5. customThe precipitate is collected
  6. washwashed with diethyl ether
  7. customThe combined precipitates

Sources & evidence

ORD record
ord-0b9671f6ef774eb186dc6ad71abbf198
Source dataset
uspto-grants-1999_09
Patent number
US05958691

Reaction notes

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