Diisopropylethylamine → (+/-)-N4-(5-cyclopropyl-1H-pyrazol-3-yl)-N2-methyl-N2-(1-(1-(tetrahydro-2H-pyran-2-yl)-1H-benzo[d]imidazol-5-yl)ethyl)pyrimidine-2,4-diamine

HRID 475204

Reaction equation

[CH3:1][NH:2][CH:3]([C:5]1[CH:19]=[CH:18][C:8]2[N:9]([CH:12]3[CH2:17][CH2:16][CH2:15][CH2:14][O:13]3)[CH:10]=[N:11][C:7]=2[CH:6]=1)[CH3:4].Cl[C:21]1[N:26]=[C:25]([NH:27][C:28]2[NH:32][N:31]=[C:30]([CH:33]3[CH2:35][CH2:34]3)[CH:29]=2)[CH:24]=[CH:23][N:22]=1.CCN(C(C)C)C(C)C>CC(O)C>[CH:33]1([C:30]2[NH:31][N:32]=[C:28]([NH:27][C:25]3[CH:24]=[CH:23][N:22]=[C:21]([N:2]([CH3:1])[CH:3]([C:5]4[CH:19]=[CH:18][C:8]5[N:9]([CH:12]6[CH2:17][CH2:16][CH2:15][CH2:14][O:13]6)[CH:10]=[N:11][C:7]=5[CH:6]=4)[CH3:4])[N:26]=3)[CH:29]=2)[CH2:35][CH2:34]1

Participants

Conditions

Temperature: 120 °C

Procedure

A tube was charged with mixture of 84 (200 mg, 0.77 mmol), 53 (181 mg, 0.77 mmol) and DIPEA (200 mg, 1.5 mmol) in IPA (5 mL), sealed and stirred at 120° C. overnight. The reaction mixture was cooled to RT and concentrated under reduced pressure. The crude residue was purified by SiO2 chromatography eluting with a MeOH/DCM gradient (5% to 15% MeOH) to afford 68 mg (19%) of (±)-N4-(5-cyclopropyl-1H-pyrazol-3-yl)-N2-methyl-N2-(1-(1-(tetrahydro-2H-pyran-2-yl)-1H-benzo[d]imidazol-5-yl)ethyl)pyrimidine-2,4-diamine (86) as white solid: MS (ESI) m/z=459.2 (M+1).

Workup

customsealed
temperatureThe reaction mixture was cooled to RT
concentrationconcentrated under reduced pressure
customThe crude residue was purified by SiO2 chromatography
washeluting with a MeOH/DCM gradient (5% to 15% MeOH)

Sources & evidence

ORD record: ord-509a0abd95fc485ebf44d9a342a30e85
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08637537B2

Linked notes

Loading…