Hydrochloric Acid → 5'-Amino-5-(2-chloroethyl)-2',5'-dideoxyuridine hydrochloride

HRID 1085535Notes

Reaction equation

HRID 1085535 reaction equation
[N:1]([CH2:4][C@H:5]1[O:9][C@@H:8]([N:10]2[CH:17]=[C:16]([CH2:18][CH2:19][Cl:20])[C:14](=[O:15])[NH:13][C:11]2=[O:12])[CH2:7][C@@H:6]1[OH:21])=[N+]=[N-].Cl>CO.[Pd].C(O)C>[ClH:20].[NH2:1][CH2:4][C@H:5]1[O:9][C@@H:8]([N:10]2[CH:17]=[C:16]([CH2:18][CH2:19][Cl:20])[C:14](=[O:15])[NH:13][C:11]2=[O:12])[CH2:7][C@@H:6]1[OH:21]

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 540023075'-Azido-2',5'-dideoxy-5-(2-chloroethyl)uridine

Product 1

HCID 679265535'-Amino-5-(2-chloroethyl)-2',5'-dideoxyuridine hydrochlorideYield 157.3%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 887MethanolSolvent2×

Procedure

0.16 g of 5'-azido-2',5'-dideoxy-5-(2-chloroethyl)uridine was dissolved in 100 ml of methanol and 1.9 ml of a 0.27M solution of hydrogen chloride in methanol was added. A slurry of 25 mg of 5% palladium-on-charcoal catalyst in 10 ml of ethanol was added under a nitrogen atmosphere and the mixture was hydrogenated at room temperature and under atmospheric pressure for 2 hours. The catalyst was removed by filtration and the filtrate was evaporated to give a solid which, after crystallization from a mixture of 15 ml of methanol and 30 ml of diethyl ether, gave 0.13 g of 5'-amino-5-(2-chloroethyl)-2',5'-dideoxyuridine hydrochloride of melting point 229°-230° C. (decomposition).

Workup

  1. customThe catalyst was removed by filtration
  2. customthe filtrate was evaporated
  3. customto give a solid which
  4. customafter crystallization
  5. additionfrom a mixture of 15 ml of methanol and 30 ml of diethyl ether

Sources & evidence

ORD record
ord-90d5e9af556a499386fbc4a51e94c55b
Source dataset
uspto-grants-1991_04
Patent number
US05010060

Reaction notes

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