4-(Aminomethyl)-N,N-dimethylaniline → 5-Bromo-N4-(5-cyclopropyl-1H-pyrazol-3-yl)-N2-(4-dimethylaminobenzyl)-pyrimidine-2,4-diamine

HRID 1514329Notes

Reaction equation

[Br:1][C:2]1[C:3]([NH:9][C:10]2[CH:14]=[C:13]([CH:15]3[CH2:17][CH2:16]3)[NH:12][N:11]=2)=[N:4][C:5](Cl)=[N:6][CH:7]=1.[CH3:18][N:19]([CH3:28])[C:20]1[CH:27]=[CH:26][C:23]([CH2:24][NH2:25])=[CH:22][CH:21]=1>C(O)CCC.C(OCC)(=O)C>[Br:1][C:2]1[C:3]([NH:9][C:10]2[CH:14]=[C:13]([CH:15]3[CH2:17][CH2:16]3)[NH:12][N:11]=2)=[N:4][C:5]([NH:25][CH2:24][C:23]2[CH:26]=[CH:27][C:20]([N:19]([CH3:28])[CH3:18])=[CH:21][CH:22]=2)=[N:6][CH:7]=1

Participants

Conditions

Temperature: 170 °C

Procedure

A mixture of 5-bromo-2-chloropyrimidin-4-yl-(5-cyclopropyl-1H-pyrazol-3-yl)-amine (313 mg, 1.00 mmol) and 4-dimethylaminobenzylamine (225 mg, 1.5 mmol) in 1-butanol (20 mL) was heated to 170° C. in a 50 mL sealed tube for 3 h. The mixture was cooled and diluted with ethyl acetate. The organic layer was washed with 2 N sodium hydroxide, water and brine and dried over sodium sulfate. The solution was concentrated, redissolved in DMF and purified by preparative reverse phase HPLC to give the desired product (124 mg, 29%) as a white solid.

Workup

customsealed tube for 3 h
temperatureThe mixture was cooled
washThe organic layer was washed with 2 N sodium hydroxide, water and brine
dry with materialdried over sodium sulfate
concentrationThe solution was concentrated
dissolutionredissolved in DMF
custompurified by preparative reverse phase HPLC

Sources & evidence

ORD record: ord-29c0644d2f18439cb0714240fff99e14
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08222256B2

Reaction notes

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