Sodium hydride → N-(9-[(2R,3R,4R,5R)-3,4-Bis{[tert-butyl(dimethyl)silyl]oxy}-5-(methoxymethyl)tetrahydro-2-furanyl]-2-{[(1-methyl-4-piperidinyl)oxy]methyl}-9H-purin-6-yl)-N-(2,2-diphenylethyl)amine

HRID 2268434Notes

Reaction equation

HRID 2268434 reaction equation
[H-].[Na+].CS([O:7][CH2:8][C:9]1[N:17]=[C:16]2[C:12]([N:13]=[CH:14][N:15]2[C@H:18]2[C@H:22]([O:23][Si:24]([C:27]([CH3:30])([CH3:29])[CH3:28])([CH3:26])[CH3:25])[C@H:21]([O:31][Si:32]([C:35]([CH3:38])([CH3:37])[CH3:36])([CH3:34])[CH3:33])[C@@H:20]([CH2:39][O:40][CH3:41])[O:19]2)=[C:11]([NH:42][CH2:43][CH:44]([C:51]2[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=2)[C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=2)[N:10]=1)(=O)=O.[CH3:57][N:58]1[CH2:63][CH2:62][CH:61](O)[CH2:60][CH2:59]1>O1CCCC1>[Si:24]([O:23][C@@H:22]1[C@H:21]([O:31][Si:32]([C:35]([CH3:36])([CH3:38])[CH3:37])([CH3:33])[CH3:34])[C@@H:20]([CH2:39][O:40][CH3:41])[O:19][C@H:18]1[N:15]1[CH:14]=[N:13][C:12]2[C:16]1=[N:17][C:9]([CH2:8][O:7][CH:61]1[CH2:62][CH2:63][N:58]([CH3:57])[CH2:59][CH2:60]1)=[N:10][C:11]=2[NH:42][CH2:43][CH:44]([C:45]1[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=1)[C:51]1[CH:52]=[CH:53][CH:54]=[CH:55][CH:56]=1)([C:27]([CH3:30])([CH3:29])[CH3:28])([CH3:26])[CH3:25]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 660484-Piperidinol, 1-methyl-HCID 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 69534109N-(9-[(2R,3R,4R,5R)-3,4-Bis{[tert-butyl(dimethyl)silyl]oxy}-5-(methoxymethyl)tetrahydro-2-furanyl]-2-{[(1-methyl-4-piperidinyl)oxy]methyl}-9H-purin-6-yl)-N-(2,2-diphenylethyl)amineYield 11.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Sodium hydride (42 mg of an 80% dispersion in mineral oil, 1.4 mmol) was added to 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 (preparation 16) (540 mg, 0.7 mmol) and 1-methyl-4-piperidinol (160 mg, 1.4 mmol) in tetrahydrofuran (10 ml). The reaction mixture was heated at reflux for 24 hr and then the solvent removed under reduced pressure to give a residue which was purified by column chromatography on silica gel eluting with dichloromethane:methanol (95:5) to give the title compound (68 mg). MS: 818 (MH+).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 24 hr
  3. customthe solvent removed under reduced pressure
  4. customto give a residue which
  5. customwas purified by column chromatography on silica gel eluting with dichloromethane:methanol (95:5)

Sources & evidence

ORD record
ord-c97c4a02620f40399e4d9aa374a1242a
Source dataset
uspto-grants-2001_12
Patent number
US06326359B1

Reaction notes

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