Carbon tetrabromide → HCID 54325433, compound

HRID 232389Notes

Reaction equation

HRID 232389 reaction equation
[C:1]([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)(=[O:3])[CH3:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[N-:39]=[N+:40]=[N-:41].[Na+].C(Br)(Br)(Br)Br>CN(C)C=O>[C:1]([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][N:39]=[N+:40]=[N-:41])[C@@H:11]([OH:12])[CH2:10]1)(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 33557Sodium AzideHCID 54136175HCID 54136175, compound

Product 1

HCID 54325433HCID 54325433, compoundYield 58.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1.26 g of 5-acetyl-2'-deoxyuridine, 1.35 g of triphenylphosphine, 1.52 g of sodium azide and 1.7 g of carbon tetrabromide in 40 ml of dimethylformamide were reacted as described in Example 54 and the product was purified by chromatography on 400 g of silica gel in dichloromethane/methanol (9:1) to give 0.80 g of 5-acetyl-5'-azido-2',5'-dideoxyuridine of melting point 159°-162° C. (decomposition).

Workup

  1. customthe product was purified by chromatography on 400 g of silica gel in dichloromethane/methanol (9:1)

Sources & evidence

ORD record
ord-5672b32c516045729e1b5ef957c44629
Source dataset
uspto-grants-1989_07
Patent number
US04851519

Reaction notes

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