Methyl iodide → 2-[(2-{4-[(4-chloro-3-methylphenyl)oxy]phenyl}ethyl)oxy]-5-ethyl-1-methyl-4(1H)-pyrimidinone

HRID 474866Notes

Reaction equation

HRID 474866 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]2[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][O:17][C:18]3[NH:19][CH:20]=[C:21]([CH2:25][CH3:26])[C:22](=[O:24])[N:23]=3)=[CH:11][CH:10]=2)=[CH:4][C:3]=1[CH3:27].[CH3:28]CN(C(C)C)C(C)C.CI>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]2[CH:10]=[CH:11][C:12]([CH2:15][CH2:16][O:17][C:18]3[N:19]([CH3:28])[CH:20]=[C:21]([CH2:25][CH3:26])[C:22](=[O:24])[N:23]=3)=[CH:13][CH:14]=2)=[CH:4][C:3]=1[CH3:27]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 81531DiisopropylethylamineHCID 178437199HCID 178437199, compound

Product 1

HCID 677756442-[(2-{4-[(4-chloro-3-methylphenyl)oxy]phenyl}ethyl)oxy]-5-ethyl-1-methyl-4(1H)-pyrimidinoneYield 25.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture solution of 2-[(2-{4-[(4-chloro-3-methylphenyl)oxy]phenyl}ethyl)oxy]-5-ethyl-4(1H)-pyrimidinone (30 mg, 0.078 mmol) and DIPEA (0.027 mL, 0.156 mmol) in DCM (2 mL) was added MeI (9.75 μL, 0.156 mmol). The mixture was stirred at room temperature for 3 h, and quenched with water. The aqueous layer was extracted with DCM. The combined organic layers was dried with anhydrous Na2SO4, filtered, concentrated, and purified via MDAP to afford the title compound (8 mg, 25.7% yield) as oil. LCMS: rt=3.56 min, [M+H+]=399

Workup

  1. customquenched with water
  2. extractionThe aqueous layer was extracted with DCM
  3. dry with materialThe combined organic layers was dried with anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. custompurified via MDAP

Sources & evidence

ORD record
ord-9e205fb41afc4130a7a5984c720a5b77
Source dataset
uspto-grants-2014_01
Patent number
US08637536B2

Reaction notes

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