p-Toluenesulfonic acid monohydrate → 2-{3-[(5-Chloro-4-{[3-(3-methoxyphenyl)propyl]amino}pyrimidin-2-yl)amino]phenyl}ethanol

HRID 1614964Notes

Reaction equation

HRID 1614964 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][CH2:9][CH2:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH3:19])[CH:13]=2)[C:5]([Cl:20])=[CH:4][N:3]=1.[NH2:21][C:22]1[CH:23]=[C:24]([CH2:28][CH2:29][OH:30])[CH:25]=[CH:26][CH:27]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>O1CCOCC1>[Cl:20][C:5]1[C:6]([NH:8][CH2:9][CH2:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH3:19])[CH:13]=2)=[N:7][C:2]([NH:21][C:22]2[CH:23]=[C:24]([CH2:28][CH2:29][OH:30])[CH:25]=[CH:26][CH:27]=2)=[N:3][CH:4]=1

Participants

5

Reactant 3

HCID 521998p-Toluenesulfonic acid monohydrateHCID 149389872-(3-Aminophenyl)ethan-1-olHCID 58467875HCID 58467875, compound

Product 1

HCID 584678952-{3-[(5-Chloro-4-{[3-(3-methoxyphenyl)propyl]amino}pyrimidin-2-yl)amino]phenyl}ethanolYield 92.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 2,5-dichloro-N-[3-(3-methoxyphenyl)propyl]pyrimidin-4-amine (0.50 g, 1.6 mmol) (prepared according to Example 10, Step A) and 2-(3-aminophenyl)ethanol (0.30 g, 2.2 mmol) (prepared according to Example 2, Step A) in 1,4-dioxane (13.6 mL) was added p-toluenesulfonic acid monohydrate (0.11 g, 0.58 mmol). The mixture was heated at 100° C. for 16 hours and the reaction was complete. After cooling, the mixture was filtered under vacuum. The cake was washed with cold EtOAc and H2O successively to give the desired product as a light brown gum (0.61 g, 92%). LCMS for C22H26ClN4O2 (M+H)+: m/z=413.1.

Workup

  1. temperatureAfter cooling
  2. filtrationthe mixture was filtered under vacuum
  3. washThe cake was washed with cold EtOAc and H2O successively

Sources & evidence

ORD record
ord-827da83daf484fc5a4d96f7041e68541
Source dataset
uspto-grants-2014_07
Patent number
US08765727B2

Reaction notes

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