Reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12]([C:13]3[CH:18]=[CH:17][N:16]=[C:15]([NH:19]CC4C=CC(OC)=CC=4)[N:14]=3)=[CH:11][NH:10][N:9]=2)=[CH:4][CH:3]=1>FC(F)(F)C(O)=O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12]([C:13]3[CH:18]=[CH:17][N:16]=[C:15]([NH2:19])[N:14]=3)=[CH:11][NH:10][N:9]=2)=[CH:4][CH:3]=1Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of 4-[3-(4-fluorophenyl)-1H-pyrazol-4-yl]-N-[(4-methoxyphenyl)methyl]-2-pyrimidinamine prepared in accordance with Example A-305 (0.35 g, 0.00093 mol) in 15 mL of trifluoroacetic acid was heated at reflux for 16 hours. Solvent was removed and the residue was partitioned between ethyl acetate and 1 N ammonia hydroxide. Organic layer was washed with brine, dried over magnesium sulfate and filtered. The filtrate was concentrated and purified by chromatography on silica gel (ethyl acetate) to give 0.14 g of product, 4-[3-(4-fluorophenyl)-1H-pyrazol-4-yl]-2-pyrimidinamine, as a pale yellow solid (59% yield), mp: 273–274° C.; Anal. Calc'd for C13H10FN5.0.25H2O: C, 60.11; H, 4.07; N, 26.96. Found: C, 60.15; H, 3.82; N, 26.38.
Workup
- temperatureat reflux for 16 hours
- customSolvent was removed
- customthe residue was partitioned between ethyl acetate and 1 N ammonia hydroxide
- washOrganic layer was washed with brine
- dry with materialdried over magnesium sulfate
- filtrationfiltered
- concentrationThe filtrate was concentrated
- custompurified by chromatography on silica gel (ethyl acetate)
Sources & evidence
- ORD record
- ord-8dc0493f10844c5bb7b9764150328538
- Source dataset
- uspto-grants-2006_12
- Patent number
- US07153959B2
Linked notes
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