Hexachloroethane → HCID 90408179, compound

HRID 1521683Notes

Reaction equation

HRID 1521683 reaction equation
[Li+].C[Si]([N-][Si](C)(C)C)(C)C.[C:11]([C:14]1[CH:36]=[CH:35][C:17]([CH2:18][N:19]2[CH:34]=[C:22]3[C:23](=[O:33])[N:24]([CH3:32])[C:25]4[N:26]([CH2:27][C:28]([CH3:31])([CH3:30])[N:29]=4)[C:21]3=[N:20]2)=[CH:16][CH:15]=1)(=[O:13])[CH3:12].[Cl:37]C(Cl)(Cl)C(Cl)(Cl)Cl>C1COCC1.C(Cl)Cl>[C:11]([C:14]1[CH:36]=[CH:35][C:17]([CH2:18][N:19]2[C:34]([Cl:37])=[C:22]3[C:23](=[O:33])[N:24]([CH3:32])[C:25]4[N:26]([CH2:27][C:28]([CH3:31])([CH3:30])[N:29]=4)[C:21]3=[N:20]2)=[CH:16][CH:15]=1)(=[O:13])[CH3:12]

Participants

6

Reactant 3

HCID 6214HexachloroethaneHCID 2733832Lithium HexamethyldisilazideHCID 90408481HCID 90408481, compound

Product 1

HCID 90408179HCID 90408179, compoundYield 43%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-20 °C

Procedure

1.0M LiHMDS (2.5 mL, 2.5 mmol) in THF is added dropwise into a solution of 7,8-dihydro-2-(4-acetylbenzyl)-5,7,7-trimethyl-[2H]-imidazo-[1,2-a]pyrazolo[4,3-e]pyrimidin-4(5H)-one (580 mg, 1.65 mmol) and hexachloroethane (782 mg, 3.32 mmol) in methylene chloride (8 mL) at −20° C. The reaction mixture is stirred at −20° C. for 30 min, and then quenched with acetic acid (60 μL). Solvents are removed under reduced pressure and the obtained residue is purified on a basic alumina oxide column to give 273 mg of product (yield: 43%). MS (ESI) m/z 386.2 [M+H]+.

Workup

  1. customquenched with acetic acid (60 μL)
  2. customSolvents are removed under reduced pressure
  3. customthe obtained residue is purified on a basic alumina oxide column

Sources & evidence

ORD record
ord-6e323fec54d44862837e7875d8e571d8
Source dataset
uspto-grants-2015_07
Patent number
US09073936B2

Reaction notes

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