Methyl iodide → HCID 86607298, compound

HRID 552697Notes

Reaction equation

HRID 552697 reaction equation
[Cl:1][C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[C@@H:11]1[O:21][C@H:20]2[C@@H:13]([O:14][Si:15]([CH:31]([CH3:33])[CH3:32])([CH:28]([CH3:30])[CH3:29])[O:16][Si:17]([CH:25]([CH3:27])[CH3:26])([CH:22]([CH3:24])[CH3:23])[O:18][CH2:19]2)[C@@H:12]1[OH:34].[C:35]([O-])([O-])=O.[Cs+].[Cs+].CI>CN(C=O)C>[Cl:1][C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[C@@H:11]1[O:21][C@H:20]2[C@@H:13]([O:14][Si:15]([CH:28]([CH3:30])[CH3:29])([CH:31]([CH3:33])[CH3:32])[O:16][Si:17]([CH:25]([CH3:26])[CH3:27])([CH:22]([CH3:23])[CH3:24])[O:18][CH2:19]2)[C@@H:12]1[O:34][CH3:35]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 86607299HCID 86607299, compound

Product 1

HCID 86607298HCID 86607298, compoundYield 71.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of (6aR,8R,9S,9aS)-8-(6-chloro-9H-purin-9-yl)-2,2,4,4-tetraisopropyltetrahydro-6H-furo[3,2-f][1,3,5,2,4]trioxadisilocin-9-ol (300 mg, 0.57 mmol) and Cs2CO3 (1.86 g, 5.7 mmol) in DMF (5.7 mL) at 0° C. was added MeI (350 μL, 5.7 mmol) dropwise. The suspension was stirred for 3 hours, quenched with saturated aqueous NH4Cl and CH2Cl2. The layers were separated and the aqueous layer was extracted with CH2Cl2 (2×). The combined organic layers were dried over Na2SO4, filtered, and concentrated in vacuo. The crude material was purified by silica gel chromatography (0 to 20% EtOAc/hexanes) to afford 221 mg (71%) of the title compound.

Workup

  1. customquenched with saturated aqueous NH4Cl and CH2Cl2
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted with CH2Cl2 (2×)
  4. dry with materialThe combined organic layers were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude material was purified by silica gel chromatography (0 to 20% EtOAc/hexanes)

Sources & evidence

ORD record
ord-e7a77919ac0a4e19a9bc3bf62e001951
Source dataset
uspto-grants-2011_05
Patent number
US07951810B2

Reaction notes

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