Methyl iodide → HCID 86607298, compound

HRID 552754Notes

Reaction equation

HRID 552754 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.C(Cl)Cl>[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

6

Reactant 3

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

Product 1

HCID 86607298HCID 86607298, compoundYield 48%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

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 (3.06 g, 5.79 mmol) and Cs2CO3 (18.86 g, 57.9 mmol) in DMF (58 mL) at 0° C. was added methyl iodide (3.60 mL, 57.9 mmol) dropwise and reaction was stirred for 3 h while warming to r.t. The solution was diluted with CH2Cl2 (150 mL) and washed with saturated aq NH4Cl. The aq layer was extracted with CH2Cl2 (2×100 mL) and the combined organics were dried (Na2SO4), filtered, and concentrated. The crude material was purified by flash chromatography (5 to 30% EtOAc/hexanes) to afford the title compound (1.51 g, 48%).

Workup

  1. customreaction
  2. washwashed with saturated aq NH4Cl
  3. extractionThe aq layer was extracted with CH2Cl2 (2×100 mL)
  4. dry with materialthe combined organics were dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude material was purified by flash chromatography (5 to 30% EtOAc/hexanes)

Sources & evidence

ORD record
ord-5af3c2a795f84533afbe6c1e058a35e2
Source dataset
uspto-grants-2011_05
Patent number
US07951810B2

Reaction notes

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