Ammonia → Ammonia

HRID 2372517Notes

Reaction equation

HRID 2372517 reaction equation
[NH2:1][C@@H]1[C@@H](CO)O[C@@H](N2C=CC(N)=NC2=O)C1.C([O:20][CH2:21][C@H:22]1[O:26][C@@H:25]([N:27]2[CH:34]=[CH:33][C:31](=O)[NH:30][C:28]2=[O:29])[CH2:24][C@@H:23]1[N:35]=[N+:36]=[N-:37])(=O)C.ClC1C=CC([ClH]P(Cl)(=O)[O-])=CC=1.[NH:50]1C=NC=N1.N>N1C=CC=CC=1.O1CCOCC1>[NH3:1].[N:35]([C@@H:23]1[C@@H:22]([CH2:21][OH:20])[O:26][C@@H:25]([N:27]2[CH:34]=[CH:33][C:31]([NH2:50])=[N:30][C:28]2=[O:29])[CH2:24]1)=[N+:36]=[N-:37]

Participants

8

Reactant 4

HCID 222AmmoniaHCID 92571H-1,2,4-TriazoleHCID 7351584472-90-2HCID 1371196984472-87-7

Product 2

HCID 222AmmoniaHCID 451374Cytidine, 3'-azido-2',3'-dideoxy-

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 312751,4-DioxaneSolvent

Procedure

An alternate synthesis of compound (XIII) involves treatment of 3'-azido-5'-O-acetyl-2',3'-dideoxyuridine (X) with 4-chlorophenylphosphorodichloridate and 1,2,4-triazole in pyridine at room temperature for 3 days to give the 4-trizolylpyrimidinone derivative. Subsequent treatment with aqueous ammonia in dioxane (1:3 v/v) for 4 hours, then saturated methanolic ammonia overnight at room temperature, yields the 3'-azido analog (XII) Compound (XII) is then reduced under 50 psi of hydrogen in the presence of 10% palladium on charcoal at room temperature for 6 hours to obtain the desired 3'amino-2',3'-dideoxycytidine derivative (XIII).

Workup

  1. customat room temperature
  2. customfor 3 days
  3. customto give the 4-trizolylpyrimidinone derivative

Sources & evidence

ORD record
ord-cd688450c20d42c9ad4b92700fdb23ee
Source dataset
uspto-grants-1992_03
Patent number
US05099010

Reaction notes

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