Dichloromethane → 4-Chloro-7-[2-c-methyl-3,5-bis-o-(2,4-dichlorophenylmethyl)-beta-d-ribofuranosyl]-5-(2-hydroxyethyl)-7h-pyrrolo[2,3-d]pyrimidine

HRID 915866Notes

Reaction equation

HRID 915866 reaction equation
[O:1]([CH2:9][CH2:10][C:11]1[C:19]2[C:18]([Cl:20])=[N:17][CH:16]=[N:15][C:14]=2[N:13]([C@@H:21]2[O:36][C@H:35]([CH2:37][O:38][CH2:39][C:40]3[CH:45]=[CH:44][C:43]([Cl:46])=[CH:42][C:41]=3[Cl:47])[C@@H:24]([O:25][CH2:26][C:27]3[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][C:28]=3[Cl:34])[C@@:22]2([CH3:48])[OH:23])[CH:12]=1)[Si](C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C(Cl)Cl>C1COCC1.[Cl-].[Na+].O>[Cl:20][C:18]1[C:19]2[C:11]([CH2:10][CH2:9][OH:1])=[CH:12][N:13]([C@@H:21]3[O:36][C@H:35]([CH2:37][O:38][CH2:39][C:40]4[CH:45]=[CH:44][C:43]([Cl:46])=[CH:42][C:41]=4[Cl:47])[C@@H:24]([O:25][CH2:26][C:27]4[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][C:28]=4[Cl:34])[C@@:22]3([CH3:48])[OH:23])[C:14]=2[N:15]=[CH:16][N:17]=1

Participants

6

Reactant 3

HCID 6344DichloromethaneHCID 2724141Tetrabutylammonium FluorideHCID 875172625-[2-(Tert-butyldimethylsiloxy)ethyl]-4-chloro-7-[2-c-methyl-3,5-bis-o-(2,4-dichlorophenylmethyl)-beta-d-ribofuranosyl]-7h-pyrrolo[2,3-d]pyrimidine

Product 1

HCID 875057074-Chloro-7-[2-c-methyl-3,5-bis-o-(2,4-dichlorophenylmethyl)-beta-d-ribofuranosyl]-5-(2-hydroxyethyl)-7h-pyrrolo[2,3-d]pyrimidineYield 92.5%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of compound 2.5 (1.14 g, 1.47 mmol) in THF (30 mL) was added a 1.0M solution of tetrabutylammonium fluoride in THF (2.2 mmol) at room temperature. The colorless solution was stirred for 5 hr at room temperature and then diluted by addition of 10 mL of CH2Cl2 and 10 mL of brine. The aqueous layer was extracted three times with CH2Cl2, dried over Na2SO4, filtered and evaporated. The residue obtained was purified by silica gel column chromatography using 1-1.5% MeOH in CH2Cl2 as eluent to give the desired compound 2.6 (900 mg, 88%) as a white solid.

Workup

  1. extractionThe aqueous layer was extracted three times with CH2Cl2
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. customevaporated
  5. customThe residue obtained
  6. customwas purified by silica gel column chromatography

Sources & evidence

ORD record
ord-bd6cffc26bef4a1681c49fd7a46262ab
Source dataset
uspto-grants-2007_09
Patent number
US07268119B2

Reaction notes

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