Methyl iodide → 2-[({4-[(4-fluorophenyl)oxy]phenyl}methyl)thio]-1-methyl-5-{[2-(methyloxy)-5-pyrimidinyl]methyl}-4(1H)-pyrimidinone

HRID 706036Notes

Reaction equation

HRID 706036 reaction equation
[F:1][C:2]1[CH:32]=[CH:31][C:5]([O:6][C:7]2[CH:30]=[CH:29][C:10]([CH2:11][S:12][C:13]3[NH:14][CH:15]=[C:16]([CH2:20][C:21]4[CH:22]=[N:23][C:24]([O:27][CH3:28])=[N:25][CH:26]=4)[C:17](=[O:19])[N:18]=3)=[CH:9][CH:8]=2)=[CH:4][CH:3]=1.[CH3:33]CN(C(C)C)C(C)C.CI>C(Cl)Cl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][C:7]2[CH:30]=[CH:29][C:10]([CH2:11][S:12][C:13]3[N:14]([CH3:33])[CH:15]=[C:16]([CH2:20][C:21]4[CH:26]=[N:25][C:24]([O:27][CH3:28])=[N:23][CH:22]=4)[C:17](=[O:19])[N:18]=3)=[CH:9][CH:8]=2)=[CH:31][CH:32]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 81531DiisopropylethylamineHCID 178494157HCID 178494157, compound

Product 1

HCID 677752742-[({4-[(4-fluorophenyl)oxy]phenyl}methyl)thio]-1-methyl-5-{[2-(methyloxy)-5-pyrimidinyl]methyl}-4(1H)-pyrimidinoneYield 29.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 2-(4-(4-fluorophenoxy)benzylthio)-5-((2-methoxypyrimidin-5-yl)methyl) pyrimidin-4(1H)-one (100 mg, 0.222 mmol) and Hunig's base (0.058 mL, 0.333 mmol) in DCM (4 mL) was added MeI (0.021 mL, 0.333 mmol). The mixture was heated at 50° C. for 2 h. Purification via reverse phase flash chromatography then afforded the title compound (30 mg, 29.1% yield). LCMS: rt=3.05 min, [M+H]=465.

Workup

  1. customPurification via reverse phase flash chromatography

Sources & evidence

ORD record
ord-d59cee155f5841eaae920315d510025d
Source dataset
uspto-grants-2015_11
Patent number
US09174968B2

Reaction notes

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