Triethylamine → (S)-tert-butyl 4-((2-(4-(3-cyclopropylureido)phenyl)-4-(3-methylmorpholino)-5H-pyrrolo[3,4-d]pyrimidin-6(7H)-yl)methyl)piperidine-1-carboxylate

HRID 1626641Notes

Reaction equation

[CH:1]1([NH:4][C:5]([NH:7][C:8]2[CH:13]=[CH:12][C:11]([C:14]3[N:15]=[C:16]([N:23]4[CH2:28][CH2:27][O:26][CH2:25][C@@H:24]4[CH3:29])[C:17]4[CH2:22][NH:21][CH2:20][C:18]=4[N:19]=3)=[CH:10][CH:9]=2)=[O:6])[CH2:3][CH2:2]1.C(N(CC)CC)C.Br[CH2:38][CH:39]1[CH2:44][CH2:43][N:42]([C:45]([O:47][C:48]([CH3:51])([CH3:50])[CH3:49])=[O:46])[CH2:41][CH2:40]1>CN(C=O)C>[CH:1]1([NH:4][C:5](=[O:6])[NH:7][C:8]2[CH:9]=[CH:10][C:11]([C:14]3[N:15]=[C:16]([N:23]4[CH2:28][CH2:27][O:26][CH2:25][C@@H:24]4[CH3:29])[C:17]4[CH2:22][N:21]([CH2:38][CH:39]5[CH2:44][CH2:43][N:42]([C:45]([O:47][C:48]([CH3:49])([CH3:51])[CH3:50])=[O:46])[CH2:41][CH2:40]5)[CH2:20][C:18]=4[N:19]=3)=[CH:12][CH:13]=2)[CH2:2][CH2:3]1

Participants

Conditions

Temperature: 75 °C

Procedure

To a solution of (S)-1-cyclopropyl-3-(4-(4-(3-methylmorpholino)-6,7-dihydro-5H-pyrrolo[3,4-d]pyrimidin-2-yl)phenyl)urea (Example 3) (147 mg, 0.37 mmol) and triethyamine (52 μL, 0.37 mmol) in DMF (3 mL, anhydrous) was added tert-butyl 4-(bromomethyl)piperidine-1-carboxylate (103 mg, 0.37 mmol). The reaction mixture was stirred at 75° C. until LCMS indicated reaction was complete. Solvent was then removed in vacuo. Purified by prep. HPLC (high pH) to afford a brown solid (28.9 mg, 0.049 mmol, 13%).

Workup

customreaction
customSolvent was then removed in vacuo
customPurified by prep

Sources & evidence

ORD record: ord-114a5e73b1144cc6884a96236e4af592
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08785457B2

Reaction notes

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