Dimethylformamide → 2-[2-(Isopropylamino-methyl)-pyrrolidin-1-yl]-3-methyl-6-pyridin-4-yl-5-(3-vinyl-phenyl)-3H-pyrimidin-4-one

HRID 1795452Notes

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.[C:32]1(C)C(C)=CC=C[CH:37]=1.CN(C=O)C.[F-].[K+]>ClCCl>[CH:27]([NH:26][CH2:25][CH:21]1[CH2:22][CH2:23][CH2:24][N:20]1[C:11]1[N:10]([CH3:30])[C:9](=[O:31])[C:8]([C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([CH:32]=[CH2:37])[CH:3]=2)=[C:13]([C:14]2[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=2)[N:12]=1)([CH3:29])[CH3:28]

Participants

Conditions

Temperature: 140 °C

Procedure

To a 250 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 (0.48 g, 1.0 mmol), 50 mL xylene, 5 mL DMF and 0.58 mL tributhyl(vinyl)tin. The mixture was degassed by nitrogen bubbled through for 1 h. After added Pd(PPh)4 (58 mg, 0.05 mmol), the mixture was warmed up to 140° C. and stirred for 1 h under nitrogen. The mixture was cooled down to rt, 20 mL 10% KF solution was added and stirred for 30 min. The mixture was diluted with 200 mL dichloromethane, washed with sat. NaHCO3 and brine. After purified by flash chromatography, the title compound was obtained in 0.28 g as pale yellow solid. MS (ES+): 430 (M+H)+; (ES−): 428 (M−H).

Workup

customThe mixture was degassed by nitrogen
custombubbled through for 1 h
temperatureThe mixture was cooled down to rt
stirringstirred for 30 min
washwashed with sat. NaHCO3 and brine
customAfter purified by flash chromatography

Sources & evidence

ORD record: ord-0ed289cdc0b3462fbeb15b3e17302beb
Source dataset: uspto-grants-2006_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07026326B2

Reaction notes

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