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

HRID 706038Notes

Reaction equation

HRID 706038 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.CCN(C(C)C)[CH:36]([CH3:38])[CH3:37].BrCCC>ClCCCl>[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]([CH2:37][CH2:36][CH3:38])[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 78401-BromopropaneHCID 81531DiisopropylethylamineHCID 178494157HCID 178494157, compound

Product 1

HCID 677759572-[({4-[(4-fluorophenyl)oxy]phenyl}methyl)thio]-5-{[2-(methyloxy)-5-pyrimidinyl]methyl}-1-propyl-4(1H)-pyrimidinoneYield 31.4%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

The same procedure as E54 from 2-((4-(4-fluorophenoxy)benzyl)thio)-5-((2-methoxypyrimidin-5-yl)methyl)pyrimidin-4(1H)-one (146.6 mg, 0.325 mmol), Hunig's base (0.171 mL, 0.976 mmol) and 1-bromopropane (80 mg, 0.651 mmol) in DCE (5 mL), except that the time was prolonged to 3 days, to afford the title compound (50 mg, 0.102 mmol, 31.2% yield). LCMS: rt=3.41 min, [M+H+]=493

Sources & evidence

ORD record
ord-35c5ff23c0b74302afeff6cee364d65a
Source dataset
uspto-grants-2015_11
Patent number
US09174968B2

Reaction notes

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