Water → HCID 11188940, compound
Reaction equation
[F:1][C:2]([F:21])([F:20])[C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10]2[C:11]3[CH2:19][CH2:18][NH:17][CH2:16][C:12]=3[N:13]=[CH:14][N:15]=2)=[CH:5][CH:4]=1.Cl[C:23]1[C:28]([Cl:29])=[CH:27][CH:26]=[CH:25][N:24]=1.C(N(CC)C(C)C)(C)C.O>O1CCOCC1.CN(C)C(=O)C>[Cl:29][C:28]1[C:23]([N:17]2[CH2:18][CH2:19][C:11]3[C:10]([NH:9][C:6]4[CH:5]=[CH:4][C:3]([C:2]([F:1])([F:20])[F:21])=[CH:8][CH:7]=4)=[N:15][CH:14]=[N:13][C:12]=3[CH2:16]2)=[N:24][CH:25]=[CH:26][CH:27]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 170 °C
Procedure
A mixture of N-(4-(trifluoromethyl)phenyl)-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-4-amine (0.250 g, 0.85 mmol), 2,3-dichloropyridine (0.251 g, 1.69 mmol) and N,N-diisopropylethylamine (0.22 mL, 1.27 mmol) in a mixture of 1,4-dioxane (2 mL) and N,N-dimethylacetamide (0.2 mL) was heated in a sealed tube via microwave (Emerys Optimizer model, Personal Chemistry) for 10 hr at 170° C. The mixture was allowed to cool to room temperature and poured into water (60 mL). The mixture was extracted with ethyl acetate (2×30 mL) and the combined organic layers were washed with brine, dried over sodium sulfate and concentrated to leave an oil. The residue was purified by flash chromatography over silica gel (ethyl acetate/hexane gradient 0 to 100%) to obtain 198 mg of a white solid.
Workup
- temperatureto cool to room temperature
- extractionThe mixture was extracted with ethyl acetate (2×30 mL)
- washthe combined organic layers were washed with brine
- dry with materialdried over sodium sulfate
- concentrationconcentrated
- customto leave an oil
- customThe residue was purified by flash chromatography over silica gel (ethyl acetate/hexane gradient 0 to 100%)
Sources & evidence
- ORD record
- ord-cba04d994c144a428643d77f7f9c9b59
- Source dataset
- uspto-grants-2007_12
- Patent number
- US07312330B2
Reaction notes
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