Chloromethyl Methyl Ether → HCID 86592276, compound

HRID 1059312Notes

Reaction equation

HRID 1059312 reaction equation
[Si:1]([O:8][CH2:9][CH2:10][C:11]1[CH:24]=[N:23][C:14]2[S:15][C:16]3[CH:22]=[CH:21][CH:20]=[CH:19][C:17]=3[NH:18][C:13]=2[N:12]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[H-].[Na+].[CH3:27][O:28][CH2:29]Cl>O1CCCC1>[O:8]([CH2:9][CH2:10][C:11]1[CH:24]=[N:23][C:14]2[S:15][C:16]3[CH:22]=[CH:21][CH:20]=[CH:19][C:17]=3[N:18]([CH2:27][O:28][CH3:29])[C:13]=2[N:12]=1)[Si:1]([C:4]([CH3:5])([CH3:6])[CH3:7])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 7864Chloromethyl Methyl EtherHCID 24758Sodium hydrideHCID 86592277HCID 86592277, compound

Product 1

HCID 86592276HCID 86592276, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

603 mg of 8-[(2-(tert-butyldimethylsilyloxy)ethyl]-10H-pyrazino[2,3-b][1,4]benzothiazine was dissolved in 6 ml of tetrahydrofuran. After adding 63 mg of 70% sodium hydride, the resulting mixture was stirred under ice-cooling for 15 minutes. Then 0.14 ml of chloromethyl methyl ether was added thereto and the resulting mixture was stirred for 1 hour and for additional 18 hours at room temperature. The reaction mixture was concentrated under reduced pressure and the residue was purified by silica gel column chromatography (eluted with n-hexane/ethyl acetate) to thereby give 463 mg of the title compound as a brown oily substance.

Workup

  1. temperaturecooling for 15 minutes
  2. stirringthe resulting mixture was stirred for 1 hour and for additional 18 hours at room temperature
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. customthe residue was purified by silica gel column chromatography (eluted with n-hexane/ethyl acetate)

Sources & evidence

ORD record
ord-c069cdab92dd4230ab7f75a21c101486
Source dataset
uspto-grants-2003_02
Patent number
US06518423B1

Reaction notes

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