Dimethyl Sulfate → HCID 22253350, compound

HRID 1612384Notes

Reaction equation

HRID 1612384 reaction equation
[CH2:1]([CH:3]([N:6]1[C:14]2[CH:13]=[C:12]([CH3:15])[N:11]=[C:10]([O:16][C:17]3[C:22]([CH3:23])=[CH:21][C:20]([CH3:24])=[CH:19][C:18]=3[CH3:25])[C:9]=2[CH2:8][C:7]1=O)[CH2:4][CH3:5])[CH3:2].[H-].[Na+].S([O:34][CH3:35])(OC)(=O)=O.[CH3:36]N(P(N(C)C)(N(C)C)=O)C>>[CH2:1]([CH:3]([N:6]1[C:14]2[CH:13]=[C:12]([CH3:15])[N:11]=[C:10]([O:16][C:17]3[C:22]([CH3:23])=[CH:21][C:20]([CH3:24])=[CH:19][C:18]=3[CH3:25])[C:9]=2[C:8]([CH3:36])=[C:7]1[O:34][CH3:35])[CH2:4][CH3:5])[CH3:2]

Participants

5

Reactant 4

HCID 6497Dimethyl SulfateHCID 12679HexamethylphosphoramideHCID 24758Sodium hydrideHCID 22253352HCID 22253352, compound

Product 1

HCID 22253350HCID 22253350, compound

Conditions

Temperature
0 °C

Procedure

To a 0° C. solution of 1-(1-Ethyl-propyl)-6-methyl-4-(2,4,6-trimethyl-phenoxy)-1,3-dihydro-pyrrolo[3,2-c]pyridin-2-one (134 mg, 0.381 mmol) in 2 ml of HMPA was added 60% sodium hydride in oil (20 mg, 0.5 mmol) and the resulting mixture was stirred at 0° C. for 10 min. Dimethyl sulfate (66.5 mg, 0.53 mmol) was added and stirred for 30 min. The reaction mixture was quenched with dilute acid to pH4 and extracted with ethyl acetate. The organic layer was washed with brine, dried and concentrated to give a clear oil. The oil was purified through silica gel column chromatography using 3% ethyl acetate in hexane as eluent to give 70 mg of the title compound as white solid. 1H NMR (CDCl3) δ 6.88(s,2H), 6.61(s,1H), 4.0(m,1H), 3.95(s,3H), 2,44(s,3H), 2.29(s,3H), 2.26(s,3H), 2.10(s,6H), 1.95–2.1(m,2H), 1.7–1.9(m,2H), 0.78(t,6H)ppm.

Workup

  1. stirringstirred for 30 min
  2. customThe reaction mixture was quenched
  3. additionwith dilute acid to pH4
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with brine
  6. customdried
  7. concentrationconcentrated
  8. customto give a clear oil
  9. customThe oil was purified through silica gel column chromatography

Sources & evidence

ORD record
ord-f9cbb24615654f55bee932ae028f17d2
Source dataset
uspto-grants-2006_01
Patent number
US06992188B1

Reaction notes

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