Ammonia → 5-Amino-2'-deoxyuridine

HRID 420425

Reaction equation

HRID 420425 reaction equation
Br[C:2]1[C:3](=[O:17])[NH:4][C:5](=[O:16])[N:6]([CH:15]=1)[C@@H:7]1[O:14][C@H:11]([CH2:12][OH:13])[C@@H:9]([OH:10])[CH2:8]1.[NH3:18]>>[NH2:18][C:2]1[C:3](=[O:17])[NH:4][C:5](=[O:16])[N:6]([CH:15]=1)[C@@H:7]1[O:14][C@H:11]([CH2:12][OH:13])[C@@H:9]([OH:10])[CH2:8]1

Participants

3

Reactant 2

HCID 222AmmoniaHCID 60355-Bromo-2'-deoxyuridine2×

Product 1

HCID 1110815-Amino-2'-deoxyuridine

Procedure

5-amino-2′-deoxyuridine was prepared from 5-bromo-2′-deoxyuridine according to the procedure of Roberts and Visser, J. Am. Chem. Soc. 14:665-669 (1952). 5-bromo-2′-deoxyuridine (2 g, 6.2 mmol) dissolved in liquid ammonia (20 ml) was scaled in a glass tube and heated at 50° for 5 days. The tube was opened, and the ammonia was evaporated. 5-amino-2′-deoxyuridine was recrystallized from 5 ml water and 75 ml hot isopropyl alcohol.

Workup

  1. customwas scaled in a glass tube
  2. temperatureheated at 50° for 5 days
  3. customthe ammonia was evaporated
  4. custom5-amino-2′-deoxyuridine was recrystallized from 5 ml water and 75 ml hot isopropyl alcohol

Sources & evidence

ORD record
ord-95e6653125404c8eaa8121ec929f44b0
Source dataset
uspto-grants-2012_01
Patent number
US08097405B1

Linked notes

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