1-[(4R,6S,6aR)-6-(iodomethyl)-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl]-5-fluoropyrimidine-2,4-dione → 5'-Deoxy-5'-iodo-5-fluorouridine

HRID 1358066Notes

Reaction equation

HRID 1358066 reaction equation
CC1(C)[O:9][CH:8]2[C@H:4]([C@@H:5]([CH2:19][I:20])[O:6][C@H:7]2[N:10]2[C:16](=[O:17])[NH:15][C:13](=[O:14])[C:12]([F:18])=[CH:11]2)[O:3]1>C(O)(=O)C.O>[I:20][CH2:19][C@H:5]1[O:6][C@@H:7]([N:10]2[CH:11]=[C:12]([F:18])[C:13](=[O:14])[NH:15][C:16]2=[O:17])[C@H:8]([OH:9])[C@@H:4]1[OH:3]

Participants

4

Reactant 1

HCID 453585381-[(4R,6S,6aR)-6-(iodomethyl)-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl]-5-fluoropyrimidine-2,4-dione

Product 1

HCID 108723875'-Deoxy-5'-iodo-5-fluorouridineYield 77.3%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Conditions

Temperature
95 °C

Procedure

A suspension of 51 g (0.105 m) of 5′-deoxy-5′-iodo-2′,3′-O-isopropylidene-5-fluorouridine in 500 ml of acetic acid and 120 ml of water is heated at 95° C. for 90 minutes. The solution thus obtained is concentrated under vacuum and the residue is taken up with 2 l of ethyl acetate, then is concentrated to a small volume and, after 15 hours at room temperature, the precipitate is filtered, washed with ethyl acetate and dried to give 35.6 g of 5′-deoxy-5′-iodo-5-fluoro uridine. M.p.=174.5÷175.5° C., purity (HPLC)=99.74% [α]D=+8.96° (c=1.00, CH3OH).

Workup

  1. customThe solution thus obtained
  2. concentrationis concentrated under vacuum
  3. concentrationis concentrated to a small volume and, after 15 hours at room temperature
  4. filtrationthe precipitate is filtered
  5. washwashed with ethyl acetate
  6. customdried

Sources & evidence

ORD record
ord-9a67032000eb4f7fb845dc99c386eac5
Source dataset
uspto-grants-2003_07
Patent number
US06593467B2

Reaction notes

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