Ammonia → HCID 54212246, compound

HRID 1108421Notes

Reaction equation

HRID 1108421 reaction equation
[NH2:1][C:2]1[C:3]2[N:10]=[N:9][N:8]([C@@H:11]3[O:17][C@H:16]([CH2:18][OH:19])[C@@H:14]([OH:15])[C@H:12]3[OH:13])[C:4]=2[N:5]=[CH:6][N:7]=1.C[Si](Cl)(C)C.[C:25](Cl)(=[O:32])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.N>N1C=CC=CC=1.O>[C:25]([NH:1][C:2]1[C:3]2[N:10]=[N:9][N:8]([C@@H:11]3[O:17][C@H:16]([CH2:18][OH:19])[C@@H:14]([OH:15])[C@H:12]3[OH:13])[C:4]=2[N:5]=[CH:6][N:7]=1)(=[O:32])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

7

Reactant 4

HCID 222AmmoniaHCID 6397ChlorotrimethylsilaneHCID 7412Benzoyl chlorideHCID 9641010299-44-2

Product 1

HCID 54212246HCID 54212246, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1049PyridineSolvent

Procedure

100 mg (0.37 mmol) of 7-amino-3-β-D-ribofuranosyl-3H-1,2,3-triazolo[4,5-d]pyrimidine are initially introduced in 5 ml of dry pyridine. 0.47 ml (3.7 mmol) of trimethylsilyl chloride is added dropwise to this solution under an argon atmosphere. After the mixture has been stirred at room temperature for half an hour (monitoring by TLC), 0.25 ml (2.0 mmol) of benzoyl chloride is added dropwise, and this reaction mixture is stirred at room temperature for 4 hours. It is then cooled down to 0-5° C. and 1 ml of water is added followed, 5 min later, by 2 ml of aqueous ammonia (25%); this mixture is then stirred for a further 30 min. The solvent is stripped off and the residue is then evaporated with toluene. The residue is taken up in 15 ml of a saturated solution of NaHCO3, and this mixture is extracted one with 25 ml of methylene chloride and several times with ethyl acetate. The combined organic phases are dried using Na2SO4.

Workup

  1. additionis added dropwise
  2. temperatureIt is then cooled down to 0-5° C.
  3. waitfollowed, 5 min
  4. stirringthis mixture is then stirred for a further 30 min
  5. customthe residue is then evaporated with toluene
  6. extractionthis mixture is extracted one with 25 ml of methylene chloride and several times with ethyl acetate
  7. customThe combined organic phases are dried

Sources & evidence

ORD record
ord-03415ceb00a045de96a93575ff80d45f
Source dataset
uspto-grants-2000_05
Patent number
US06066720

Reaction notes

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