Diisopropylethylamine → N4-(5-cyclopropyl-1H-pyrazol-3-yl)-N2-(1-(3-(4-methoxybenzyl)-3H-imidazo[4,5-c]pyridin-6-yl)ethyl)pyrimidine-2,4-diamine

HRID 2409079Notes

Reaction equation

Cl[C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:13]=[C:12]([CH:14]3[CH2:16][CH2:15]3)[NH:11][N:10]=2)[CH:5]=[CH:4][N:3]=1.[CH3:17][O:18][C:19]1[CH:37]=[CH:36][C:22]([CH2:23][N:24]2[C:28]3[CH:29]=[N:30][C:31]([CH:33]([NH2:35])[CH3:34])=[CH:32][C:27]=3[N:26]=[CH:25]2)=[CH:21][CH:20]=1.CCN(C(C)C)C(C)C>CC(C(O)C(C)C)C>[CH:14]1([C:12]2[NH:11][N:10]=[C:9]([NH:8][C:6]3[CH:5]=[CH:4][N:3]=[C:2]([NH:35][CH:33]([C:31]4[N:30]=[CH:29][C:28]5[N:24]([CH2:23][C:22]6[CH:36]=[CH:37][C:19]([O:18][CH3:17])=[CH:20][CH:21]=6)[CH:25]=[N:26][C:27]=5[CH:32]=4)[CH3:34])[N:7]=3)[CH:13]=2)[CH2:16][CH2:15]1

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of 2-chloro-N-(5-cyclopropyl-1H-pyrazol-3-yl)pyrimidin-4-amine (167 mg, 0.71 mmol), 1-(3-(4-methoxybenzyl)-3H-imidazo[4,5-c]pyridin-6-yl)ethanamine (200 mg, 0.71 mmol), DIPEA (275 mg, 2.31 mmol) in 2,4-dimethylpentan-3-ol (3.0 mL) in a sealed tube was heated at 120° C. overnight. The reaction mixture was concentrated under reduced pressure and the residue purified by SiO2 chromatography eluting with DCM/MeOH (15:1) to 135 mg (61%) to afford 135 mg (56%) of N4-(5-cyclopropyl-1H-pyrazol-3-yl)-N2-(1-(3-(4-methoxybenzyl)-3H-imidazo[4,5-c]pyridin-6-yl)ethyl)pyrimidine-2,4-diamine as white solid. MS (ESI): m/z=482.2[M+1]+.

Workup

concentrationThe reaction mixture was concentrated under reduced pressure
customthe residue purified by SiO2 chromatography
washeluting with DCM/MeOH (15:1) to 135 mg (61%)

Sources & evidence

ORD record: ord-8f3649cef2424f74b880ec075c0f6668
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08815877B2

Reaction notes

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