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

HRID 448694Notes

Reaction equation

HRID 448694 reaction equation
[NH2:1][C:2]1[N:3]=[C:4]([Cl:40])[C:5]2[C:10]([CH3:11])=[CH:9][N:8]([C@@H:12]3[O:27][C@H:26]([CH2:28][O:29][CH2:30][C:31]4[CH:36]=[CH:35][C:34]([Cl:37])=[CH:33][C:32]=4[Cl:38])[C@@H:15]([O:16][CH2:17][C:18]4[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][C:19]=4[Cl:25])[C@@:13]3([CH3:39])[OH:14])[C:6]=2[N:7]=1.[H-].[Na+].[CH3:43]I>C1COCC1>[NH2:1][C:2]1[N:3]=[C:4]([Cl:40])[C:5]2[C:10]([CH3:11])=[CH:9][N:8]([C@@H:12]3[O:27][C@H:26]([CH2:28][O:29][CH2:30][C:31]4[CH:36]=[CH:35][C:34]([Cl:37])=[CH:33][C:32]=4[Cl:38])[C@@H:15]([O:16][CH2:17][C:18]4[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][C:19]=4[Cl:25])[C@@:13]3([CH3:39])[O:14][CH3:43])[C:6]=2[N:7]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 872855862-Amino-4-chloro-7-[3,5-bis-O-(2,4-dichlorophenylmethyl)-2-C-methyl-beta-D-ribofuranosy]-5-methyl-7H-pyrrolo[2,3-d]pyrimidine

Product 1

HCID 235183222-Amino-4-chloro-7-[3,5-bis-o-(2,4-dichlorophenylmethyl)-2-c,2-o-dimethyl-beta-d-ribofuranosyl]-5-methyl-7h-pyrrolo[2,3-d]pyrimidine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To an ice-cold mixture of the product from Step A (475 mg, 0.7 mmol) in THF (7 mL) was added NaH (60% in mineral oil, 29 mg) and stirred at 0° C. for 0.5 h. Then MeI (48 μL) was added and reaction mixture stirred at rt for 24 h. The reaction was quenched with MeOH and the mixture evaporated. The crude product was purified on a silica gel column (5×3.5 cm) using hexane/ethyl acetate (9/1, 7/1, 5/1 and 3/1) as eluent. Fractions containing the product were combined and evaporated to give the desired compound (200 mg) as a colorless foam.

Workup

  1. customreaction mixture
  2. stirringstirred at rt for 24 h
  3. customThe reaction was quenched with MeOH
  4. customthe mixture evaporated
  5. customThe crude product was purified on a silica gel column (5×3.5 cm)
  6. additionFractions containing the product
  7. customevaporated

Sources & evidence

ORD record
ord-210b1f19d0e54a3da7c81dce39d82f47
Source dataset
uspto-grants-2013_07
Patent number
US08481712B2

Reaction notes

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