Thiophenol → 2-Fluoro-4-(2-(phenylamino)pyrimidin-5-yl)phenol

HRID 1993354Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]([C:10]2[CH:11]=[N:12][C:13]([NH:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[N:14][CH:15]=2)[CH:5]=[CH:6][C:7]=1[O:8]C.C1(S)C=CC=CC=1.C([O-])([O-])=O.[K+].[K+]>CN1C(=O)CCC1.O>[F:1][C:2]1[CH:3]=[C:4]([C:10]2[CH:15]=[N:14][C:13]([NH:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[N:12][CH:11]=2)[CH:5]=[CH:6][C:7]=1[OH:8]

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of 5-(3-fluoro-4-methoxyphenyl)-N-phenylpyrimidin-2-amine (Step 2, 0.066 g, 0.22 mmol), thiophenol (0.20 g, 1.0 mmol), and K2CO3 (0.15 g, 1.1 mmol) in NMP (2 mL) was heated at 120° C. for 20 h. The mixture was cooled to RT and diluted with H2O (4 mL). After stirring for 10 min, the resulting suspension was filtered, and the solid was further washed with H2O. The solid was washed with hexanes to provide the title compound as a brown solid. MS (ESI pos. ion) m/z: 282. Calc'd for C16H12FN3O: 281.10.

Workup

temperatureThe mixture was cooled to RT
filtrationthe resulting suspension was filtered
washthe solid was further washed with H2O
washThe solid was washed with hexanes

Sources & evidence

ORD record: ord-b925e905939943bda3fa52233e6c9381
Source dataset: uspto-grants-2010_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07652009B2

Reaction notes

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