HCID 57540555, compound → HCID 46927358, compound

HRID 2059873Notes

Reaction equation

HRID 2059873 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][CH2:9][C:10]2[N:15]=[CH:14][NH:13][C:12](=[O:16])[CH:11]=2)=[CH:4][CH:3]=1.Br[C:18]1[CH:30]=[CH:29][C:21]([O:22][CH2:23][CH:24]([CH:26]2[CH2:28][CH2:27]2)[OH:25])=[C:20]([O:31][CH3:32])[CH:19]=1>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][CH2:9][C:10]2[N:15]=[CH:14][N:13]([C:18]3[CH:30]=[CH:29][C:21]([O:22][CH2:23][CH:24]([CH:26]4[CH2:27][CH2:28]4)[OH:25])=[C:20]([O:31][CH3:32])[CH:19]=3)[C:12](=[O:16])[CH:11]=2)=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 57540555HCID 57540555, compoundHCID 136097745HCID 136097745, compound

Product 1

HCID 46927358HCID 46927358, compound

Procedure

N-arylation of 6-((4-chlorophenylthio)methyl)pyrimidin-4(3H)-one Part B of Procedure 10 with 2-(4-bromo-2-methoxyphenoxy)-1-cyclopropylethanol Part C to generate G-2 was achieved using the procedure described in Part C of Procedure 10. LC/MS 459 (M+H)+, tR 0.97 min (method 5). 1H NMR (400 MHz, Chloroform-D) δ ppm 8.14 (1H, s), 7.26-7.40 (4H, m), 7.03 (1H, d), 6.80-6.91 (2H, m), 6.45 (1H, s), 4.20 (1H, dd, J=9.54, 2.76 Hz), 4.03 (1H, t, J=8.91 Hz), 3.96 (2H, s), 3.87 (3H, s), 3.36 (1H, td, J=8.34, 2.64 Hz), 0.91-1.06 (1H, m), 0.51-0.67 (2H, m), 0.40-0.50 (1H, m), 0.26-0.37 (1H, m).

Sources & evidence

ORD record
ord-305ee4077ccb4b72a4af91088968cf86
Source dataset
uspto-grants-2012_10
Patent number
US08278316B2

Reaction notes

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