Trimethylsilyl triflate → HCID 60004402, compound

HRID 2184275Notes

Reaction equation

HRID 2184275 reaction equation
[C:1]1([CH:7]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH2:8][NH:9][C:10]2[N:18]=[C:17]([C:19]([NH:21][CH2:22][CH2:23][N:24]3[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]3)=[O:20])[N:16]=[C:15]3[C:11]=2[N:12]=[CH:13][NH:14]3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.FC(F)(F)S(O[Si](C)(C)C)(=O)=O.C(O[C@@H:52]1[O:64][C@H:63]([CH2:65][O:66][C:67](=[O:69])[CH3:68])[C@@H:58]([O:59][C:60](=[O:62])[CH3:61])[C@H:53]1[O:54][C:55](=[O:57])[CH3:56])(=O)C>COCCOC>[C:30]1([CH:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH2:8][NH:9][C:10]2[N:18]=[C:17]([C:19]([NH:21][CH2:22][CH2:23][N:24]3[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]3)=[O:20])[N:16]=[C:15]3[C:11]=2[N:12]=[CH:13][N:14]3[C@@H:52]2[O:64][C@H:63]([CH2:65][O:66][C:67](=[O:69])[CH3:68])[C@@H:58]([O:59][C:60](=[O:62])[CH3:61])[C@H:53]2[O:54][C:55](=[O:57])[CH3:56])[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

5

Reactant 3

HCID 65367Trimethylsilyl triflateHCID 830641,2,3,5-Tetraacetyl-beta-D-ribofuranoseHCID 1785234056-[(2,2-Diphenylethyl)amino]-N-[2-(1-piperidinyl)ethyl]-9H-purine-2-carboxamide

Product 1

HCID 60004402HCID 60004402, compound

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent3×

Conditions

Temperature
60 °C

Procedure

To a stirred suspension of 6-[(2,2-diphenylethyl)amino]-N-[2-(1-piperidinyl)ethyl]-9H-purine-2-carboxamide (200 g, 0.426 moles) (Preparation 23) in anhydrous 1,2-dimethoxyethane (800 ml) under an atmosphere of nitrogen was added a solution of trimethylsilyl trifluoromethanesulfonate (200 g, 0.900 moles) in anhydrous 1,2-dimethoxyethane (200 ml) over a period of 15 minutes. During the addition, all the solid dissolved to give a deep red/amber solution and the reaction temperature rose from 20° C. to 31.5° C. The resultant mixture was heated to 55-60° C. and a solution of 1,2,3,5-tetra-O-acetyl-β-D-ribofuranose (163 g, 0.512 moles) in anhydrous 1,2-dimethoxyethane (400 ml) was added over a period of 40 minutes. The addition apparatus was rinsed through into the reaction mixture with anhydrous 1,2-dimethoxyethane (200 ml). The reaction mixture was heated at 60° C. for 3 hours and was allowed to cool to ambient temperature. This crude reaction solution was held at ambient temperature for 18 hours. The resulting mixture containing the title compound may be used directly without further purification.

Workup

  1. additionDuring the addition
  2. dissolutionall the solid dissolved
  3. customto give a deep red/amber solution
  4. customrose from 20° C. to 31.5° C
  5. washThe addition apparatus was rinsed through into the reaction mixture with anhydrous 1,2-dimethoxyethane (200 ml)
  6. temperatureto cool to ambient temperature
  7. customThis crude reaction solution

Sources & evidence

ORD record
ord-6be52401d2884cf69ff5ddbac42f8f06
Source dataset
uspto-grants-2005_05
Patent number
US06900309B1

Reaction notes

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