4-Chlorobenzyl mercaptan → 4-(4-chlorobenzylthio)-1-(4-(2-hydroxy-2-methylpropoxy)-3-methoxyphenyl)pyrimidin-2(1H)-one

HRID 2059842Notes

Reaction equation

[OH:1][C:2]([CH3:23])([CH3:22])[CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH:16]=[CH:15][C:14]([S:17][CH3:18])=[N:13][C:12]2=[O:19])=[CH:7][C:6]=1[O:20][CH3:21].[Cl:24][C:25]1[CH:30]=[CH:29][C:28](CS)=[CH:27][CH:26]=1>C(Cl)Cl>[Cl:24][C:25]1[CH:30]=[CH:29][C:28]([CH2:18][S:17][C:14]2[CH:15]=[CH:16][N:11]([C:8]3[CH:9]=[CH:10][C:5]([O:4][CH2:3][C:2]([OH:1])([CH3:23])[CH3:22])=[C:6]([O:20][CH3:21])[CH:7]=3)[C:12](=[O:19])[N:13]=2)=[CH:27][CH:26]=1

Participants

Conditions

Temperature: 145 °C

Procedure

A mixture of 1-(4-(2-hydroxy-2-methylpropoxy)-3-methoxyphenyl)-4-(methylthio)pyrimidin-2(1H)-one (90 mg, 0.268 mmol) and (4-chlorophenyl)methanethiol (707 μl, 5.35 mmol) was heated to 145° C. (neat) for 30 min. The mixture was diluted with methylene chloride, washed with water, dried (Na2SO4) and concentrated. The crude product was subjected to ISCO flash chromatography (silica gel/hexanes:ethyl acetate 100:0 to 0:100 gradient) to afford the title compound 4-(4-chlorobenzylthio)-1-(4-(2-hydroxy-2-methylpropoxy)-3-methoxyphenyl)pyrimidin-2(1H)-one A-1 (83.5 mg, 0.187 mmol, 69.8% yield) as a yellow solid. LC/MS 447 (M+H)+, tR 0.93 (method 5); 1H NMR (400 MHz, chloroform-D) δ 7.33-7.44 (3H, m), 7.24-7.31 (2H, m), 6.91-6.99 (2H, m), 6.86 (1H, dd, J=8.53, 2.51 Hz), 6.24 (1H, d, J=7.03 Hz), 4.48 (2H, s), 3.86 (3H, s), 3.85 (2H, s), 1.35 (6H, s).

Workup

washwashed with water
dry with materialdried (Na2SO4)
concentrationconcentrated

Sources & evidence

ORD record: ord-267baea3db4846d0b4f0fbf554fdf866
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08278316B2

Reaction notes

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