Trifluoroacetic acid → 5-bromo-N2-(1,5-dimethyl-1H-pyrazol-4-yl)-N4-methylpyrimidine-2,4-diamine

HRID 1503302

Reaction equation

[Br:1][C:2]1[C:3]([NH:9][CH3:10])=[N:4][C:5](Cl)=[N:6][CH:7]=1.[CH3:11][N:12]1[C:16]([CH3:17])=[C:15]([NH2:18])[CH:14]=[N:13]1.C(O)(C(F)(F)F)=O>COCCO>[Br:1][C:2]1[C:3]([NH:9][CH3:10])=[N:4][C:5]([NH:18][C:15]2[CH:14]=[N:13][N:12]([CH3:11])[C:16]=2[CH3:17])=[N:6][CH:7]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a mixture of 5-bromo-2-chloro-N-methylpyrimidin-4-amine (0.201 g, 0.903 mmol) and 1,5-dimethyl-1H-pyrazol-4-amine (0.12 g, 1.08 mmol) in 2-methoxyethanol (2 mL) was added TFA (0.070 mL, 0.9 mmol). The reaction was stirred in a sealed tube at 100° C. for 90 minutes. The resulting precipitate was collected by filtration. The isolated solid was further purified by reverse phase HPLC to give 5-bromo-N2-(1,5-dimethyl-1H-pyrazol-4-yl)-N4-methylpyrimidine-2,4-diamine (46 mg, 17%). LCMS (Method A): [MH+]=297.0 at 2.57 min. 1H-NMR (DMSO): δ 8.28 (s, 1H), 7.84 (s, 1H), 7.49 (s, 1H), 6.79 (d, J=3.4, 1H), 3.67 (s, 3H), 2.82 (d, J=3.6, 3H), 2.14 (s, 3H). Ki=0.017 μM.

Workup

filtrationThe resulting precipitate was collected by filtration
customThe isolated solid was further purified by reverse phase HPLC

Sources & evidence

ORD record: ord-83710fec73074483a813934e434f68f9
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09212173B2

Linked notes

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