Methyl iodide → 4-Chloro-7-[3,5-bis-o-(2,4-dichlorophenylmethyl)-2-c,2-o-dimethyl-beta-d-ribofuranosyl]-7h-pyrrolo[2,3-d]pyrimidine

HRID 2252695Notes

Reaction equation

HRID 2252695 reaction equation
[Cl:1][C:2]1[C:3]2[CH:10]=[CH:9][N:8]([C@@H:11]3[O:26][C@H:25]([CH2:27][O:28][CH2:29][C:30]4[CH:35]=[CH:34][C:33]([Cl:36])=[CH:32][C:31]=4[Cl:37])[C@@H:14]([O:15][CH2:16][C:17]4[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][C:18]=4[Cl:24])[C@@:12]3([CH3:38])[OH:13])[C:4]=2[N:5]=[CH:6][N:7]=1.[CH3:39]I.[H-].[Na+].[Cl-].[NH4+]>C1COCC1.ClCCl>[Cl:1][C:2]1[C:3]2[CH:10]=[CH:9][N:8]([C@@H:11]3[O:26][C@H:25]([CH2:27][O:28][CH2:29][C:30]4[CH:35]=[CH:34][C:33]([Cl:36])=[CH:32][C:31]=4[Cl:37])[C@@H:14]([O:15][CH2:16][C:17]4[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][C:18]=4[Cl:24])[C@@:12]3([CH3:38])[O:13][CH3:39])[C:4]=2[N:5]=[CH:6][N:7]=1

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 114449314-Chloro-7-[3,5-bis-o-(2,4-dichlorobenzyl)-2-c-methyl-beta-d-ribofuranosyl]-7h-pyrrolo[2,3-d]pyrimidine

Product 1

HCID 235183384-Chloro-7-[3,5-bis-o-(2,4-dichlorophenylmethyl)-2-c,2-o-dimethyl-beta-d-ribofuranosyl]-7h-pyrrolo[2,3-d]pyrimidineYield 116.3%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a pre-cooled (0° C.) solution of the compound from Example 2, Step D (618 mg, 1.0 mmol) in THF (8 mL) was added methyl iodide (709 mg, 5.0 mmol) and NaH (60% in mineral oil) (44 mg, 1.1 mmol). The resulting mixture was stirred overnight at room temperature and then poured into a stirred mixture of saturated aqueous ammonium chloride (50 mL) and dichloromethane (50 mL). The organic layer was washed with water (50 mL), dried (MgSO4) and evaporated in vacuo. The resulting crude product was purified on silica gel using ethyl acetate/hexane as the eluent. Fractions containing the product were pooled and evaporated in vacuo to give the desired product (735 mg) as a colorless foam.

Workup

  1. washThe organic layer was washed with water (50 mL)
  2. dry with materialdried (MgSO4)
  3. customevaporated in vacuo
  4. customThe resulting crude product was purified on silica gel
  5. additionFractions containing the product
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-66c34a17b96847aa8ef45d0ecd90a6e9
Source dataset
uspto-grants-2008_01
Patent number
US07323453B2

Reaction notes

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