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

HRID 706037Notes

Reaction equation

HRID 706037 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][CH2:34]N(C(C)C)C(C)C.C(I)C>ClCCCl>[CH2:33]([N:14]1[CH:15]=[C:16]([CH2:20][C:21]2[CH:26]=[N:25][C:24]([O:27][CH3:28])=[N:23][CH:22]=2)[C:17](=[O:19])[N:18]=[C:13]1[S:12][CH2:11][C:10]1[CH:29]=[CH:30][C:7]([O:6][C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:32][CH:31]=2)=[CH:8][CH:9]=1)[CH3:34]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 81531DiisopropylethylamineHCID 178494157HCID 178494157, compound

Product 1

HCID 677758881-ethyl-2-[({4-[(4-fluorophenyl)oxy]phenyl}methyl)thio]-5-{[2-(methyloxy)-5-pyrimidinyl]methyl}-4(1H)-pyrimidinoneYield 5.64%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
55 °C

Procedure

To a solution of 2-((4-(4-fluorophenoxy)benzyl)thio)-5-((2-methoxypyrimidin-5-yl)methyl)pyrimidin-4(1H)-one (167 mg, 0.371 mmol) in DCE (5 mL) was added Hunig's base (0.194 mL, 1.112 mmol) and EtI (0.045 mL, 0.556 mmol). The mixture was heated at 55° C. for 2 days. Purification via reverse phase flash chromatography then afforded the title compound (10 mg, 5.64% yield). LCMS: rt=3.24 min, [M+H+]=479

Workup

  1. customPurification via reverse phase flash chromatography

Sources & evidence

ORD record
ord-2647eea8cac2438f8a696ec1b97b4ae4
Source dataset
uspto-grants-2015_11
Patent number
US09174968B2

Reaction notes

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