Methyl iodide → HCID 9836515, compound

HRID 448655Notes

Reaction equation

HRID 448655 reaction equation
[NH2:1][C:2]1[N:3]=[C:4]([Cl:20])[C:5]2[CH:10]=[CH:9][N:8]([C@@H:11]3[O:17][C@H:16]([CH2:18][OH:19])[C@@H:14]([OH:15])[C@H:12]3[OH:13])[C:6]=2[N:7]=1.[H-].[Na+].I[CH3:24]>CN(C=O)C>[NH2:1][C:2]1[N:3]=[C:4]([Cl:20])[C:5]2[CH:10]=[CH:9][N:8]([C@@H:11]3[O:17][C@H:16]([CH2:18][OH:19])[C@@H:14]([OH:15])[C@H:12]3[O:13][CH3:24])[C:6]=2[N:7]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 11174104HCID 11174104, compound

Product 1

HCID 9836515HCID 9836515, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of the compound from Step B (1.0 g, 3.3 mmol) in dry DMF (100 mL) at 15° C. was treated with 60% NaH (0.14 g, 3.5 mmol). After 30 min., iodomethane (47 g, 3.3 mmol) was added portionwise to the stirred solution. The reaction was stirred at room temperature for 16 hrs. and then evaporated at a temperature below 40° C. The resulting solid was chromatographed on silica gel to afford the product as a white solid; yield 0.81 g. 1H NMR (DMSO-d6): δ 3.25 (s, 3H), 3.54 (m, 2H), 3.87 (m, 1H), 4.07 (m, 1H), 4.22 (m, 1H), 5.01 (m, 1H), 5.16 (d, 1H), 6.07 (d, 1H), 6.37 (d, 1H), 6.70 (s br, 2H), 7.40 (s, 1H). Mass spectrum: m/z 316 (M+1)+.

Workup

  1. customand then evaporated at a temperature below 40° C
  2. customThe resulting solid was chromatographed on silica gel

Sources & evidence

ORD record
ord-4eddfe13095d4752a3a023966081ca1c
Source dataset
uspto-grants-2013_07
Patent number
US08481712B2

Reaction notes

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