Water → [6-(3-Methoxyphenyl)-2-(morpholin-4-ylethyl)pyrimidin-4-yl]-3-pyridylamine

HRID 30446Notes

Reaction equation

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

Participants

Conditions

Temperature: 60 °C

Procedure

Compound 15 (1 eq) is dissolved in 3 ml of dimethyl acetamide and morpholine (5 eq) is added. The reaction mixture is stirred at 60° C. for 4 h, then cooled down to room temperature. Water is added to the mixture and the crash out is filtered off, washed with water and purified by reverse phase preparatory HPLC, obtaining [6-(3-methoxyphenyl)-2-(morpholin-4-ylethyl)pyrimidin-4-yl]-3-pyridylamine 16.

Workup

temperaturecooled down to room temperature
filtrationthe crash out is filtered off
washwashed with water
custompurified by reverse phase preparatory HPLC

Sources & evidence

ORD record: ord-1b27a57977ce47bf84e62f21ee4e10f9
Source dataset: uspto-grants-2008_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07423148B2

Reaction notes

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