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

HRID 475195

Reaction equation

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

Participants

Conditions

Temperature: 120 °C

Procedure

A tube was charged with 53 (846 mg, 3.6 mmol), 68 (880 mg, 3.6 mmol), DIPEA (5 mL) and IPA (10 mL), degassed, sealed and then heated at 120° C. overnight. The solvent was evaporated in vacuo to afford 444 mg (27%) N4-(5-cyclopropyl-1H-pyrazol-3-yl)-N2-methyl-N2-((1-(tetrahydro-2H-pyran-2-yl)-1H-benzo[d]imidazol-5-yl)methyl)-pyrimidine-2,4-diamine (70) as a yellow solid; MS (ESI) m/z=445.2 [M+1]+.

Workup

customdegassed
customsealed
customThe solvent was evaporated in vacuo

Sources & evidence

ORD record: ord-819352b515fb40c7a38ac84ad72f34b0
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08637537B2

Linked notes

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