Methyl iodide → HCID 67801973, compound

HRID 706033Notes

Reaction equation

HRID 706033 reaction equation
[N:1]1[CH:6]=[C:5]([CH2:7][C:8]2[C:9](=[O:33])[N:10]=[C:11]([CH2:14][CH2:15][C:16]3[CH:21]=[CH:20][C:19]([O:22][C:23]4[CH:28]=[CH:27][CH:26]=[C:25]([C:29]([F:32])([F:31])[F:30])[CH:24]=4)=[CH:18][CH:17]=3)[NH:12][CH:13]=2)[CH:4]=[N:3][CH:2]=1.CI.[CH3:36]CN(C(C)C)C(C)C>C(Cl)Cl>[CH3:36][N:12]1[CH:13]=[C:8]([CH2:7][C:5]2[CH:6]=[N:1][CH:2]=[N:3][CH:4]=2)[C:9](=[O:33])[N:10]=[C:11]1[CH2:14][CH2:15][C:16]1[CH:17]=[CH:18][C:19]([O:22][C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([C:29]([F:32])([F:30])[F:31])[CH:24]=2)=[CH:20][CH:21]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 81531DiisopropylethylamineHCID 178517735HCID 178517735, compound

Product 1

HCID 67801973HCID 67801973, compoundYield 42.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To the solution of 5-(pyrimidin-5-ylmethyl)-2-(4-(3-(trifluoromethyl)phenoxy)phenethyl) pyrimidin-4(1H)-one (200 mg, 0.442 mmol) in DCM (10 mL) was added MeI (4.42 mL, 4.42 mmol) (1.0 M in DCM) and DIPEA (0.772 mL, 4.42 mmol) at 25° C. The mixture was stirred at room temperature for 2 days. The solvent was removed in vacuo. Purification via MDAP then afforded the title compound (87.6 mg, 40.8% yield) as a white solid. LCMS: rt=1.59 min, [M+H+]=467.

Workup

  1. customThe solvent was removed in vacuo
  2. customPurification via MDAP

Sources & evidence

ORD record
ord-1bdd03f5cb514327be812b87c4244141
Source dataset
uspto-grants-2015_11
Patent number
US09174968B2

Reaction notes

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