Carbon tetrabromide → 5'-Azido-2',5'-dideoxy-5-(2-chloroethyl)uridine

HRID 232365

Reaction equation

HRID 232365 reaction equation
[Cl:1][CH2:2][CH2:3][C:4]1[C:5](=[O:19])[NH:6][C:7](=[O:18])[N:8]([CH:17]=1)[C@@H:9]1[O:16][C@H:13]([CH2:14]O)[C@@H:11]([OH:12])[CH2:10]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[N-:39]=[N+:40]=[N-:41].[Li+].C(Br)(Br)(Br)Br>CN(C)C=O.CO>[N:39]([CH2:14][C@H:13]1[O:16][C@@H:9]([N:8]2[CH:17]=[C:4]([CH2:3][CH2:2][Cl:1])[C:5](=[O:19])[NH:6][C:7]2=[O:18])[CH2:10][C@@H:11]1[OH:12])=[N+:40]=[N-:41]

Participants

7

Reactant 4

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 88163Lithium azideHCID 5148145-(2-Chloroethyl)-2'-deoxyuridine

Product 1

HCID 540023075'-Azido-2',5'-dideoxy-5-(2-chloroethyl)uridineYield 31.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 6228DimethylformamideSolvent

Procedure

1.4 g of 5-(2-chloroethyl)-2'-deoxyuridine and 1.3 g of triphenylphosphine were dissolved in 20 ml of dimethylformamide and stirred while 1.2 g of lithium azide were added to give a solution within 5 minutes at room temperature. 1.7 g of carbon tetrabromide were added portionwise during 5 minutes to give a hazy orange colored solution which was stirred at room temperature for 17 hours. 5 ml of methanol were added to give a clear solution. After 0.5 hour, the solvents were removed by evaporation under an oil pump vacuum to give a gum which was partitioned between 30 ml of ethyl acetate and 20 ml of water. The white solid which formed was removed by filtration to give 0.64 g of crude product of melting point 179°-182° C. (decomposition). This crude product was stirred with methanol and then removed by filtration to give 0.48 g of pure 5'-azido-2',5'-dideoxy-5-(2-chloroethyl)-uridine of melting point 197°-199° C. (decomposition).

Workup

  1. additionwere added
  2. customto give a solution within 5 minutes at room temperature
  3. customto give a hazy orange colored solution which
  4. customto give a clear solution
  5. waitAfter 0.5 hour
  6. customthe solvents were removed by evaporation under an oil pump vacuum
  7. customto give a gum which
  8. customwas partitioned between 30 ml of ethyl acetate and 20 ml of water
  9. customThe white solid which formed
  10. customwas removed by filtration
  11. customto give 0.64 g of crude product of melting point 179°-182° C. (decomposition)
  12. customremoved by filtration

Sources & evidence

ORD record
ord-104589e5e70540d595c331276c191bfc
Source dataset
uspto-grants-1989_07
Patent number
US04851519

Linked notes

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