Pyridine → HCID 86594936, compound

HRID 2120059Notes

Reaction equation

HRID 2120059 reaction equation
[Na+].[P:2]([O:10][CH2:11][C@H:12]1[O:16][C@@H:15]([N:17]2[C:26]3[N:25]=[CH:24][N:23]=[C:21]([NH2:22])[C:20]=3[N:19]=[CH:18]2)[C@H:14]([OH:27])[C@@H:13]1[OH:28])([O:5][P:6]([O-:9])([O-:8])=[O:7])(=[O:4])[O-:3].[Na+].[Na+].N1C=CC=CC=1.[CH3:37][Si:38](Cl)([CH3:40])[CH3:39]>ClCCl>[P:2]([O:10][CH2:11][C@H:12]1[O:16][C@@:15]([Si:38]([CH3:40])([CH3:39])[CH3:37])([N:17]2[C:26]3[N:25]=[CH:24][N:23]=[C:21]([NH2:22])[C:20]=3[N:19]=[CH:18]2)[C@H:14]([OH:27])[C@@H:13]1[OH:28])([O:5][P:6]([OH:8])([OH:9])=[O:7])(=[O:3])[OH:4]

Participants

5

Reactant 3

HCID 1049PyridineHCID 6397ChlorotrimethylsilaneHCID 12797869Adenosine 5′-(trihydrogen diphosphate), trisodium salt

Product 1

HCID 86594936HCID 86594936, compoundYield 98.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a 500 mL round-bottomed flask was added 3 g (21.7 mmol) adenosine-5′-diphosphate sodium salt and 200 mL pyridine. After the salt had dissolved. the solution was cooled to 0° C. under nitrogen atmosphere. Trimethylsilyl chloride (85 g, 800 mmol) in 200 mL dichloromethane was added slowly to the solution. After this addition was complete, the reaction was stirred at 35° C. for 8 hr. The pyridine hydrochloride salt was removed by filtration and excess pyridine and dichloromethane removed under high vacuum for 24 hr to yield 19.3 g (21.3 mmol) of TMS-ADP. The product was used without further purification. This synthesis is illustrated in FIG. 4E.

Workup

  1. dissolutionAfter the salt had dissolved
  2. additionAfter this addition
  3. customThe pyridine hydrochloride salt was removed by filtration and excess pyridine and dichloromethane
  4. customremoved under high vacuum for 24 hr

Sources & evidence

ORD record
ord-732c1ec22efa4d498053b3d49f60d810
Source dataset
uspto-grants-2004_02
Patent number
US06689760B1

Reaction notes

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