Ammonia → Deoxyuridine

HRID 1589896Notes

Reaction equation

HRID 1589896 reaction equation
C([O:4][C@@H:5]1[C@@H:9]([CH2:10][O:11]C(=O)C)[O:8][C@@H:7]([N:15]2[CH:22]=[CH:21][C:19](=[O:20])[NH:18][C:16]2=[O:17])[C@@H:6]1Br)(=O)C.C([SnH](CCCC)CCCC)CCC.C([Sn](Cl)(CCCC)CCCC)CCC.[BH4-].[Na+].N>C(O)C>[C@@H:7]1([N:15]2[CH:22]=[CH:21][C:19](=[O:20])[NH:18][C:16]2=[O:17])[O:8][C@H:9]([CH2:10][OH:11])[C@@H:5]([OH:4])[CH2:6]1

Participants

7

Reactant 5

HCID 222AmmoniaHCID 5948TributylstannaneHCID 15096Tributyltin ChlorideHCID 4311764Sodium borohydrideHCID 11728884HCID 11728884, compound

Product 1

HCID 13712Deoxyuridine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

For example, addition of excess acetyl bromide (3.2 eq) plus 30% HBr in acetic acid (1.2 eq) to uridine at 55°-60° C. gave the desired 3',5'-di-O-acetyl-2'-bromo-2'-deoxyuridine 2 (FIG. 1; X=O in uridine and uridine derivatives) in excellent yield (>95%). 3',4'-Di-O-acetyl-2'-bromo-2'-deoxyuridine 2 was then reduced to 3 by tributyltin hydride (provided either as the premade compound or prepared by in situ generation through the reaction of tributyltin chloride with sodium borohydride) in absolute ethanol in excellent yield (>95%). 2',3'-Di-O-acetyl-2'-deoxyuridine was treated with methanolic ammonia to obtain an excellent yield of 2'-deoxyuridine. The overall yield of this process was 72-76% without chromatography.

Workup

  1. customprovided either as the premade compound
  2. customin excellent yield (>95%)

Sources & evidence

ORD record
ord-3e69e577acb64cef9a96f2c968bc2968
Source dataset
uspto-grants-1993_04
Patent number
US05200514

Reaction notes

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