tert-butyl 3-((2-(2-isopropyl-1H-benzo[d]imidazol-1-yl)-4-morpholinopyrido[3,2-d]pyrimidin-6-yl)methylene)azetidine-1-carboxylate → tert-Butyl 3-((2-(2-isopropyl-1H-benzo[d]imidazol-1-yl)-4-morpholinopyrido[3,2-d]pyrimidin-6-yl)methyl)azetidine-1-carboxylate

HRID 2091852Notes

Reaction equation

[CH:1]([C:4]1[N:8]([C:9]2[N:10]=[C:11]([N:31]3[CH2:36][CH2:35][O:34][CH2:33][CH2:32]3)[C:12]3[N:18]=[C:17]([CH:19]=[C:20]4[CH2:23][N:22]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:21]4)[CH:16]=[CH:15][C:13]=3[N:14]=2)[C:7]2[CH:37]=[CH:38][CH:39]=[CH:40][C:6]=2[N:5]=1)([CH3:3])[CH3:2]>CO>[CH:1]([C:4]1[N:8]([C:9]2[N:10]=[C:11]([N:31]3[CH2:36][CH2:35][O:34][CH2:33][CH2:32]3)[C:12]3[N:18]=[C:17]([CH2:19][CH:20]4[CH2:21][N:22]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:23]4)[CH:16]=[CH:15][C:13]=3[N:14]=2)[C:7]2[CH:37]=[CH:38][CH:39]=[CH:40][C:6]=2[N:5]=1)([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 60 °C

Procedure

tert-butyl 3-((2-(2-isopropyl-1H-benzo[d]imidazol-1-yl)-4-morpholinopyrido[3,2-d]pyrimidin-6-yl)methylene)azetidine-1-carboxylate (0.2 g) was brought up in MeOH (20 mL) and the flask was purged with nitrogen before addition of 10% Palladium on Carbon (20 mol %). The reaction was heated at 60° C. for 6 hours, cooled and filtered thru celite to obtain the crude tert-butyl 3-((2-(2-isopropyl-1H-benzo[d]imidazol-1-yl)-4-morpholinopyrido[3,2-d]pyrimidin-6-yl)methyl)azetidine-1-carboxylate following solvent evaporation.

Workup

customthe flask was purged with nitrogen before addition of 10% Palladium on Carbon (20 mol %)
temperaturecooled
filtrationfiltered
customto obtain
customthe crude tert-butyl 3-((2-(2-isopropyl-1H-benzo[d]imidazol-1-yl)-4-morpholinopyrido[3,2-d]pyrimidin-6-yl)methyl)azetidine-1-carboxylate following solvent evaporation

Sources & evidence

ORD record: ord-936b57b8e05343f38ce151e9f01d02d5
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08440651B2

Reaction notes

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