Pyridine → N6-Benzoyladenosine

HRID 2082276Notes

Reaction equation

HRID 2082276 reaction equation
C([CH:9]([OH:59])[C@@:10]1(C(=O)C2C=CC=CC=2)[O:14][C@@:13](C(=O)C2C=CC=CC=2)([N:15]2[C:24]3[N:23]=[CH:22][N:21]=[C:19]([NH2:20])[C:18]=3[N:17]=[CH:16]2)[C@:12](C(=O)C2C=CC=CC=2)([OH:33])[C@:11]1(C(=O)C1C=CC=CC=1)[OH:42])(=O)C1C=CC=CC=1.C[O-:61].[Na+].[NH+]1[CH:68]=[CH:67][CH:66]=[CH:65][CH:64]=1.N1[CH:74]=[CH:73]C=CC=1>CO.O>[C:64]([NH:20][C:19]1[C:18]2[N:17]=[CH:16][N:15]([C:24]=2[N:23]=[CH:22][N:21]=1)[C@@H:13]1[O:14][C@H:10]([CH2:9][OH:59])[C@@H:11]([OH:42])[C@H:12]1[OH:33])(=[O:61])[C:65]1[CH:74]=[CH:73][CH:68]=[CH:67][CH:66]=1

Participants

7

Reactant 4

HCID 1049PyridineHCID 4989215PyridiniumHCID 10942334Sodium MethoxideHCID 131717784HCID 131717784, compound

Product 1

HCID 11728391N6-BenzoyladenosineYield 83%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of 7.88 g (10 mmole) of the pentabenzoyl adenosine (1A) in 150 ml dry pyridine and 50 ml dry MeOH was treated with 50 ml 1M sodium methylate solution. After 15 min the solution was poured onto an ice cold solution of a 110 ml DOWEX ion exchanger 50×4 (pyridinium form) in ca 20 ml water. After 5 h stirring the pH was 5.5-6.0. After filtering from the ion exchanger, the residue was washed with boiling MeOH/water (3/1). The filtrate was evaporated to dryness and crystallized from MeOH/water 2/1 to give 3.25 g (83%) of the product as colorless needles, m.p. 151°-153° C.

Workup

  1. filtrationAfter filtering from the ion exchanger
  2. washthe residue was washed with boiling MeOH/water (3/1)
  3. customThe filtrate was evaporated to dryness
  4. customcrystallized from MeOH/water 2/1

Sources & evidence

ORD record
ord-3dc3f3847fa04fed91be4c89f0b257df
Source dataset
uspto-grants-1993_02
Patent number
US05188897

Reaction notes

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