Methyl iodide → HCID 22063735, compound

HRID 1828463Notes

Reaction equation

HRID 1828463 reaction equation
[OH:1][CH2:2]/[CH:3]=[CH:4]/[C:5]1[C:10](=[O:11])[N:9]2[CH:12]=[CH:13][C:14]([CH2:16][CH2:17][C:18]3[S:19][CH:20]=[C:21]([CH:23]([CH3:25])[CH3:24])[N:22]=3)=[CH:15][C:8]2=[N:7][C:6]=1[N:26]1[CH2:31][CH2:30][O:29][CH2:28][CH2:27]1.[CH2:32]([Zn]CC)C.CCCCCC.IC.[Cl-].[NH4+]>ClCCl>[OH:1][CH2:2][CH:3]1[CH2:32][CH:4]1[C:5]1[C:10](=[O:11])[N:9]2[CH:12]=[CH:13][C:14]([CH2:16][CH2:17][C:18]3[S:19][CH:20]=[C:21]([CH:23]([CH3:25])[CH3:24])[N:22]=3)=[CH:15][C:8]2=[N:7][C:6]=1[N:26]1[CH2:31][CH2:30][O:29][CH2:28][CH2:27]1

Participants

7

Reactant 5

HCID 6328Methyl iodideHCID 8058HexaneHCID 25517Ammonium ChlorideHCID 22063619HCID 22063619, compoundHCID 178418750HCID 178418750, compound

Product 1

HCID 22063735HCID 22063735, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-[(E)-3-Hydroxy-1-propenyl]-8-[2-(4-isopropyl-1,3-thiazol-2-yl)ethyl]-2-morpholino-4H-pyrido[1,2-a]pyrimidin-4-one (81 mg, 0.18 mmol) was added with dichloromethane (3 ml) and a solution of diethyl zinc in hexane (1.02 M, 270 μl, 0.275 mmol) and subsequently added dropwise with iodomethane (30 μl, 0.366 mmol) at room temperature. After the reaction solution was stirred for 2 hours, the reaction was stopped with saturated aqueous ammonium chloride, and the reaction solution was extracted with chloroform. The organic layer was dried over magnesium sulfate and concentrated under reduced pressure. The resulting residue was purified by thin layer silica gel chromatography (chloroform:methanol=15:1) to obtain 61 mg (73%) of the title compound.

Workup

  1. extractionthe reaction solution was extracted with chloroform
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe resulting residue was purified by thin layer silica gel chromatography (chloroform:methanol=15:1)

Sources & evidence

ORD record
ord-736d77570e624b119e0d0cd7b3bde43e
Source dataset
uspto-grants-2006_06
Patent number
US07056917B2

Reaction notes

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