Cyclopropylboronic acid → 5-(3-Cyclopropyl-phenyl)-2-[2-(isopropylamino-methyl)-pyrrolidin-1-yl]-3-methyl-6-pyridin-4-yl-3H-pyrimidin-4-one

HRID 1795453Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]([C:8]2[C:9](=[O:31])[N:10]([CH3:30])[C:11]([N:20]3[CH2:24][CH2:23][CH2:22][CH:21]3[CH2:25][NH:26][CH:27]([CH3:29])[CH3:28])=[N:12][C:13]=2[C:14]2[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=2)[CH:5]=[CH:6][CH:7]=1.[CH:32]1(B(O)O)[CH2:34][CH2:33]1.CC([O-])(C)C.[Na+]>C1(C)C=CC=CC=1>[CH:32]1([C:2]2[CH:3]=[C:4]([C:8]3[C:9](=[O:31])[N:10]([CH3:30])[C:11]([N:20]4[CH2:24][CH2:23][CH2:22][CH:21]4[CH2:25][NH:26][CH:27]([CH3:29])[CH3:28])=[N:12][C:13]=3[C:14]3[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=3)[CH:5]=[CH:6][CH:7]=2)[CH2:34][CH2:33]1

Participants

Conditions

Temperature: 100 °C

Procedure

To a 100 mL RBF, was added 5-(3-bromo-phenyl)-2-[2-(isopropylamino-methyl)-pyrrolidin-1-yl]-3-methyl-6-pyridin-4-yl-3H-pyrimidin-4-one (0.4 g, 0.82 mmol), 30 mL toluene, and cyclopropyl boronic cid (86 mg, 1.0 mmol). The mixture was degassed by nitrogen bubbled through for 1 h. After added Pd(PPh)4 (30 mg, 0.025 mmol) and NaOtBu (0.24 g, 2.5 mmol), the mixture was warmed up to 100° C. and stirred for 1 h under nitrogen. The mixture was cooled down to rt, and vacuumed down all volatile composites. After purified by flash chromatography, the title compound was obtained in 0.1 g as pale yellow solid. MS (ES+): 444 (M+H)+; (ES−): 4442 (M−H).

Workup

customThe mixture was degassed by nitrogen
custombubbled through for 1 h
temperatureThe mixture was cooled down to rt
customAfter purified by flash chromatography

Sources & evidence

ORD record: ord-010c414a4d3e43709ada671eae91efa8
Source dataset: uspto-grants-2006_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07026326B2

Reaction notes

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