3,5-Dimethoxyaniline → N4-quinolin-3-yl-N2-(3,5-dimethoxyphenyl)pyrimidine-2,4-diamine

HRID 495452Notes

Reaction equation

Cl[C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:10]=[N:11][C:12]3[C:17]([CH:18]=2)=[CH:16][CH:15]=[CH:14][CH:13]=3)[CH:5]=[CH:4][N:3]=1.[CH3:19][O:20][C:21]1[CH:22]=[C:23]([CH:25]=[C:26]([O:28][CH3:29])[CH:27]=1)[NH2:24].N(CC)(CC)CC.FC(C(O)=O)(F)F>CS(C)=O>[N:11]1[C:12]2[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:18]=[C:9]([NH:8][C:6]2[CH:5]=[CH:4][N:3]=[C:2]([NH:24][C:23]3[CH:25]=[C:26]([O:28][CH3:29])[CH:27]=[C:21]([O:20][CH3:19])[CH:22]=3)[N:7]=2)[CH:10]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of (2-chloro-pyrimidin-4-yl)-quinolin-3-yl-amine (70 mg 0.272 mmol) and 3,5-dimethoxyaniline (42 mg, 0.274 mmol) was suspended in a sealed tube with 0.3 mL of a solution of DMSO containing Et3N-TFA (50 mg). The resulting mixture was heated at 100° C. for 3 h, cooled to RT, diluted with 0.4 mL DMSO and purified via preparative HPLC to give N4-quinolin-3-yl-N2-(3,5-dimethoxyphenyl)pyrimidine-2,4-diamine as a yellow solid. M+H—374. Calc'd for C21H19N5O2: 373.414.

Workup

temperaturecooled to RT
custompurified via preparative HPLC

Sources & evidence

ORD record: ord-e0a431e501e24efab01b55bacd8164b6
Source dataset: uspto-grants-2005_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06939874B2

Reaction notes

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