Diisopropylethylamine → N4-(5-cyclopropyl-1H-pyrazol-3-yl)-N2-(1H-indol-4-ylmethyl)-N2-(3-pyridylmethyl)pyrimidine-2,4-diamine

HRID 475309Notes

Reaction equation

[NH:1]1[C:9]2[C:4](=[C:5]([CH2:10][NH:11][CH2:12][C:13]3[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=3)[CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.Cl[C:20]1[N:25]=[C:24]([NH:26][C:27]2[CH:31]=[C:30]([CH:32]3[CH2:34][CH2:33]3)[NH:29][N:28]=2)[CH:23]=[CH:22][N:21]=1.CCN(C(C)C)C(C)C>C(O)CCC>[CH:32]1([C:30]2[NH:29][N:28]=[C:27]([NH:26][C:24]3[CH:23]=[CH:22][N:21]=[C:20]([N:11]([CH2:10][C:5]4[CH:6]=[CH:7][CH:8]=[C:9]5[C:4]=4[CH:3]=[CH:2][NH:1]5)[CH2:12][C:13]4[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=4)[N:25]=3)[CH:31]=2)[CH2:34][CH2:33]1

Participants

Conditions

Temperature: 140 °C

Procedure

A 5 mL microwave tube was charged with N-(1H-indol-4-ylmethyl)-1-(3-pyridyl)methanamine (200 mg, 0.843 mmol, 2 equiv.), 2-chloro-N-(5-cyclopropyl-1H-pyrazol-3-yl)pyrimidin-4-amine (100 mg, 0.424 mmol) and n-butanol (1.2 mL). DIPEA (5 equiv., 276.98 mg, 2.1216 mmol, 0.371 mL) was added, and the reaction mixture was heated to 140° C. for 17 h in an oil bath. The reaction was filtered and the solvent was evaporated in vacuo. The residue was purified by preparative HPLC to afford 5836 mg (32%) of N4-(5-cyclopropyl-1H-pyrazol-3-yl)-N2-(1H-indol-4-ylmethyl)-N2-(3-pyridylmethyl)pyrimidine-2,4-diamine (II-10) as a light brown solid.

Workup

filtrationThe reaction was filtered
customthe solvent was evaporated in vacuo
customThe residue was purified by preparative HPLC

Sources & evidence

ORD record: ord-eddf5c25726241f8b355d687df327ce7
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08637537B2

Reaction notes

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