Urea → 4-(4-Fluorophenyl)-N-[3-(4-fluorophenyl)-1H-indazol-5-yl]-6-methyl-2-oxo-1,2,3,4-tetrahydro-5-pyrimidinecarboxamide

HRID 227702Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([NH:17][C:18](=[O:23])[CH2:19][C:20](=O)[CH3:21])[CH:15]=3)[NH:10][N:9]=2)=[CH:4][CH:3]=1.[NH2:24][C:25]([NH2:27])=[O:26].FC(F)F.[Yb].[F:33][C:34]1[CH:41]=[CH:40][C:37]([CH:38]=O)=[CH:36][CH:35]=1>C(#N)C.O>[F:33][C:34]1[CH:41]=[CH:40][C:37]([CH:38]2[C:19]([C:18]([NH:17][C:14]3[CH:15]=[C:16]4[C:11](=[CH:12][CH:13]=3)[NH:10][N:9]=[C:8]4[C:5]3[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=3)=[O:23])=[C:20]([CH3:21])[NH:27][C:25](=[O:26])[NH:24]2)=[CH:36][CH:35]=1

Participants

Conditions

Temperature: 100 °C

Procedure

The product from Step (e) (0.3 g, 0.96 mmol), urea (87 mg, 1.44 mmol) and Ytterbium trifluoromethane (60 mg, 0.096 mmol) were combined In acetonitrile (2 ml) and 4-fluorobenzaldehyde (0.1 ml, 0.96 mmol) was added. The reaction mixture was sealed and heated to 100° C. for 3 hours. The reaction was diluted with water (1 ml) and the solid product was collected by filtration. The solid was washed three times with 1:1 Et2O/CH3CN. The crude was purified by silica gel chromatography eluting with 10% MeOH in CH2Cl2 to afford the title compound, (0.15 g, 34%); MS (ES+) m/e 460 [M+H]+.

Workup

customThe reaction mixture was sealed
filtrationthe solid product was collected by filtration
washThe solid was washed three times with 1:1 Et2O/CH3CN
customThe crude was purified by silica gel chromatography
washeluting with 10% MeOH in CH2Cl2

Sources & evidence

ORD record: ord-3e22a7a9a5cf4a37ab1949b8609c2f7c
Source dataset: uspto-grants-2009_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07560467B2

Reaction notes

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