Dimethylformamide → 1-(5-Tert-Butyl-2-Methoxy-Phenyl)-3-[4-(2-Methyl-Pyrimidin-4-Yloxy)-Naphthalen-1-Yl]-Urea

HRID 23539Notes

Reaction equation

[C:1]([C:5]1[CH:6]=[CH:7][C:8]([O:33][CH3:34])=[C:9]([NH:11][C:12]([NH:14][C:15]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[C:18]([O:25][C:26]3[CH:31]=[CH:30][N:29]=[C:28](Cl)[N:27]=3)=[CH:17][CH:16]=2)=[O:13])[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].[CH3:35]N(C=O)C>COCCOC.O.CCO.C([O-])([O-])=O.[Na+].[Na+].Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([O:33][CH3:34])=[C:9]([NH:11][C:12]([NH:14][C:15]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[C:18]([O:25][C:26]3[CH:31]=[CH:30][N:29]=[C:28]([CH3:35])[N:27]=3)=[CH:17][CH:16]=2)=[O:13])[CH:10]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 160 °C

Procedure

1-(5-tert-Butyl-2-methoxy-phenyl)-3-[4-(2-chloro-pyrimidin-4-yloxy)-naphthalen-1-yl]-urea (50 mg, 0.1 mmol) was dissolved in 0.4 mL of DMF. To this was added PdCl2(PPh3)2 (10 mol %), o-methoxyboronic acid (32 mg, 0.2 mmol) in 2 mL of DME/H2O/EtOH (7:3:2) and 0.53 mL of Na2CO3 (2M). The reaction was heated in a Smith synthesizer microwave for 3 min at 160° C. The product was concentrated on silica and purified (15-30% EtOAc-hexanes) to provide 13 mg (23%) of the title compound as an off-white foam.

Workup

concentrationThe product was concentrated on silica
custompurified (15-30% EtOAc-hexanes)

Sources & evidence

ORD record: ord-b422cee0eb6347a5b27d9f9e0d7dec55
Source dataset: uspto-grants-2005_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06852717B2

Reaction notes

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