Diethyl P-((4-fluorophenyl)methyl)phosphonate → (E)-1-(3-tert-butyl-5-(4-fluorostyryl)-4-methoxyphenyl) dihydropyrimidine-2,4(1H,3H)-dione

HRID 1924447Notes

Reaction equation

HRID 1924447 reaction equation
[C:1]([C:5]1[C:6]([O:32][CH3:33])=[C:7]([CH:21]=[C:22]([N:24]2[CH2:29][CH2:28][C:27](=[O:30])[NH:26][C:25]2=[O:31])[CH:23]=1)/[CH:8]=[CH:9]/[C:10]1[CH:15]=[CH:14][C:13](NS(C)(=O)=O)=[CH:12][CH:11]=1)([CH3:4])([CH3:3])[CH3:2].[F:34]C1C=CC(CP(=O)(OCC)OCC)=CC=1>>[C:1]([C:5]1[CH:23]=[C:22]([N:24]2[CH2:29][CH2:28][C:27](=[O:30])[NH:26][C:25]2=[O:31])[CH:21]=[C:7](/[CH:8]=[CH:9]/[C:10]2[CH:15]=[CH:14][C:13]([F:34])=[CH:12][CH:11]=2)[C:6]=1[O:32][CH3:33])([CH3:4])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 11064685Diethyl P-((4-fluorophenyl)methyl)phosphonateHCID 25234639(E)-N-(4-(3-tert-butyl-5-(2,4-dioxotetrahydropyrimidin-1(2H)-yl)-2-methoxystyryl)phenyl)methanesulfonamide

Product 1

HCID 25234642(E)-1-(3-tert-butyl-5-(4-fluorostyryl)-4-methoxyphenyl) dihydropyrimidine-2,4(1H,3H)-dione

Procedure

The title compound was prepared according the procedures described in Example 1, Part H and Example 1, Part I using the product obtained in Example 1, Part G (50 mg, 0.164 mmol) and diethyl 4-fluorobenzylphosphonate (40.5 mg, 0.164 mmol). The title compound was obtained as a solid (30 mg, 46%). 1H NMR (300 MHz, DMSO-d6): δ ppm 1.37 (s, 9H), 2.72 (t, J=6.6 Hz, 2H), 3.76 (s, 3H), 3.79 (t, =6.6 Hz, 2H), 7.21 (m, 4H), 7.30 (d, J=16.3 Hz, 1H), 7.53 (d, J=2.6 Hz, 1H), 7.73 (m, 2H), 10.35 (s, 1H).

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-f77eda5c3a574db889d96bd580630995
Source dataset
uspto-grants-2012_05
Patent number
US08178548B2

Reaction notes

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