Toluene → 4-Chloro-7-(trifluoromethyl)pyrido[3,2-d]pyrimidine
Reaction equation
[F:1][C:2]([F:15])([F:14])[C:3]1[CH:12]=[N:11][C:10]2[C:9](=O)[NH:8][CH:7]=[N:6][C:5]=2[CH:4]=1.C1(C)C=CC=CC=1.CCN(C(C)C)C(C)C.O=P(Cl)(Cl)[Cl:34]>CCOC(C)=O.O>[Cl:34][C:9]1[C:10]2[N:11]=[CH:12][C:3]([C:2]([F:15])([F:14])[F:1])=[CH:4][C:5]=2[N:6]=[CH:7][N:8]=1Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 115 °C
Procedure
A pressure bottle was charged with 7-(trifluoromethyl)pyrido[3,2-d]pyrimidin-4(3H)-one (540 mg, 2.51 mmol), toluene (10.000 mL) and Hunig's base (1.315 mL, 7.53 mmol). POCl3 (0.702 mL, 7.53 mmol) was added, and the bottle was sealed. The mixture was heated to 115° C. for 4 h. After cooling to RT, the mixture was diluted with EtOAc and water, and the layers were separated. The aqueous portion was extracted with additional EtOAc, and the combined organic portions were washed with saturated sodium bicarbonate, dried over sodium sulfate, filtered and concentrated. 4-chloro-7-(trifluoromethyl)pyrido[3,2-d]pyrimidine (560 mg, 2.397 mmol, 96% yield) was isolated as a brown solid. LC/MS (ESI+) m/z=234.0 (M+H).
Workup
- customthe bottle was sealed
- temperatureAfter cooling to RT
- customthe layers were separated
- extractionThe aqueous portion was extracted with additional EtOAc
- washthe combined organic portions were washed with saturated sodium bicarbonate
- dry with materialdried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-50e9e2826ec24a8b8e07d27e9e603d0f
- Source dataset
- uspto-grants-2016_04
- Patent number
- US09309263B2
Reaction notes
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