Potassium Cyanide → 2-{9-[(2R,3R,4R,5R)-3,4-bis{[tert-butyl(dimethyl)silyl]oxy}-5-(methoxymethyl)tetrahydro-2-furanyl]-6-[(2,2-diphenylethyl)amino]-9H-purin-2-yl}acetonitrile

HRID 2268412Notes

Reaction equation

HRID 2268412 reaction equation
CS(O[CH2:6][C:7]1[N:15]=[C:14]2[C:10]([N:11]=[CH:12][N:13]2[C@H:16]2[C@H:20]([O:21][Si:22]([C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:24])[CH3:23])[C@H:19]([O:29][Si:30]([C:33]([CH3:36])([CH3:35])[CH3:34])([CH3:32])[CH3:31])[C@@H:18]([CH2:37][O:38][CH3:39])[O:17]2)=[C:9]([NH:40][CH2:41][CH:42]([C:49]2[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=2)[C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)[N:8]=1)(=O)=O.[C-:55]#[N:56].[K+]>CN(C)C=O>[Si:22]([O:21][C@@H:20]1[C@H:19]([O:29][Si:30]([C:33]([CH3:36])([CH3:34])[CH3:35])([CH3:31])[CH3:32])[C@@H:18]([CH2:37][O:38][CH3:39])[O:17][C@H:16]1[N:13]1[CH:12]=[N:11][C:10]2[C:14]1=[N:15][C:7]([CH2:6][C:55]#[N:56])=[N:8][C:9]=2[NH:40][CH2:41][CH:42]([C:49]1[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1)[C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)([C:25]([CH3:26])([CH3:28])[CH3:27])([CH3:23])[CH3:24]

Participants

4

Reactant 2

HCID 9032Potassium CyanideHCID 86757641{9-[(2R,3R,4R,5R)-3,4-bis{[tert-butyl(dimethyl)silyl]oxy}-5-(methoxymethyl)tetrahydro-2-furanyl]-6-[(2,2-diphenylethyl)amino]-9H-purin-2-yl}methyl methanesulfonate

Product 1

HCID 695341292-{9-[(2R,3R,4R,5R)-3,4-bis{[tert-butyl(dimethyl)silyl]oxy}-5-(methoxymethyl)tetrahydro-2-furanyl]-6-[(2,2-diphenylethyl)amino]-9H-purin-2-yl}acetonitrileYield 80.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
67.5 °C

Procedure

A stirred solution of {9-[(2R,3R,4R,5R)-3,4-bis{[tert-butyl(dimethyl)silyl]oxy}-5-(methoxymethyl)tetrahydro-2-furanyl]-6-[(2,2-diphenylethyl)amino]-9H-purin-2-yl}methyl methanesulfonate (3.0 g, 3.76 mmol) (preparation 16) in anhydrous N,N-dimethylformamide (20 ml) was treated with potassium cyanide (0.37 g, 5.69 mmol) and heated to 65-70° C. for 3 hr. The mixture was cooled to room temperature and partitioned between diethyl ether and water. The organic phase was separated and the aqueous phase extracted again with diethyl ether. The combined organic solutions were then washed with brine, dried with anhydrous magnesium sulfate and the solvent removed under reduced pressure. The residue was purified by column chromatography on silica gel eluting with a solvent system of diethyl ether:pentane (1:1) to afford the title compound as a foam (2.2 g). MS: 751 (MNa+).

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. custompartitioned between diethyl ether and water
  3. customThe organic phase was separated
  4. extractionthe aqueous phase extracted again with diethyl ether
  5. washThe combined organic solutions were then washed with brine
  6. dry with materialdried with anhydrous magnesium sulfate
  7. customthe solvent removed under reduced pressure
  8. customThe residue was purified by column chromatography on silica gel eluting with a solvent system of diethyl ether:pentane (1:1)

Sources & evidence

ORD record
ord-c90b054166d543e6847807decd8fb457
Source dataset
uspto-grants-2001_12
Patent number
US06326359B1

Reaction notes

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