p-Toluenesulfonic acid monohydrate → 3-[3-({4-[(2-Bromo-5-methoxybenzyl)amino]-5-chloropyrimidin-2-yl)amino]phenyl}propan-1-ol

HRID 1614969Notes

Reaction equation

[Br:1][C:2]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][C:3]=1[CH2:4][NH:5][C:6]1[C:11]([Cl:12])=[CH:10][N:9]=[C:8](Cl)[N:7]=1.[NH2:20][C:21]1[CH:22]=[C:23]([CH2:27][CH2:28][CH2:29][OH:30])[CH:24]=[CH:25][CH:26]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>O1CCOCC1>[Br:1][C:2]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][C:3]=1[CH2:4][NH:5][C:6]1[C:11]([Cl:12])=[CH:10][N:9]=[C:8]([NH:20][C:21]2[CH:22]=[C:23]([CH2:27][CH2:28][CH2:29][OH:30])[CH:24]=[CH:25][CH:26]=2)[N:7]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of N-(2-bromo-5-methoxybenzyl)-2,5-dichloropyrimidin-4-amine (4.0 g, 11 mmol) and 3-(3-aminophenyl)propan-1-ol (2.3 g, 15 mmol, prepared according to Example 12, Step B) in 1,4-dioxane (90 mL) was added p-toluenesulfonic acid monohydrate (0.31 g, 1.6 mmol). The mixture was heated at 80° C. over two days and the reaction was complete. After cooling, the mixture was filtered under vacuum. The cake was washed with cold EtOAc to give the desired product as an off-white powder (4.35 g, 83%). LCMS for C21H22BrClN4O2 (M+H)+: m/z=477.0, 479.0.

Workup

temperatureAfter cooling
filtrationthe mixture was filtered under vacuum
washThe cake was washed with cold EtOAc

Sources & evidence

ORD record: ord-d80eac14dbc14effb0bb765b47f015bd
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08765727B2

Reaction notes

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