Methyl iodide → HCID 21098178, compound

HRID 2114752Notes

Reaction equation

HRID 2114752 reaction equation
[C:1]([O:9][C:10]1[C:11]([C:29]([O:31][CH3:32])=[O:30])=[N:12][C:13]([CH:17]2[CH2:21][CH2:20][CH2:19][N:18]2[C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])=[N:14][C:15]=1[OH:16])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:33]I>C1COCC1.C([O-])([O-])=O.[Cs+].[Cs+]>[C:1]([O:9][C:10]1[C:15](=[O:16])[N:14]([CH3:33])[C:13]([CH:17]2[CH2:21][CH2:20][CH2:19][N:18]2[C:22]([O:24][C:25]([CH3:26])([CH3:27])[CH3:28])=[O:23])=[N:12][C:11]=1[C:29]([O:31][CH3:32])=[O:30])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 6328Methyl iodideHCID 178499071HCID 178499071, compound

Product 1

HCID 21098178HCID 21098178, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 10796Cesium carbonateSolvent

Conditions

Temperature
40 °C

Procedure

To a stirred solution of the product of Step 2 (1.0 eq.) in THF, Cs2CO3 was added (1.2 eq.) followed by the addition of CH3I (2.0 eq.). The reaction was stirred at 40° C. until the starting material was consumed as determined by MS analysis. The reaction was concentrated and the residue taken up with EtOAc, washed with 1 N HCl, saturated solution of NaHCO3 and brine. The organic phase was dried over anhydrous Na2SO4, filtered and concentrated. Reaction crude showed 3.4:1 ratio N (desired product) versus O methylation. The title product was purified by flash column chromatography (EtOAc:Petroleum Ether=1:1) and obtained as a 1:1 mixture of rotamers by NMR.

Workup

  1. customwas consumed
  2. concentrationThe reaction was concentrated
  3. washwashed with 1 N HCl, saturated solution of NaHCO3 and brine
  4. dry with materialThe organic phase was dried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customReaction crude

Sources & evidence

ORD record
ord-a6cb4a9f91324ff594039beff16ce163
Source dataset
uspto-grants-2008_10
Patent number
US07435734B2

Reaction notes

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