Phosphorus oxychloride → HCID 22346599, compound
Reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9](=O)[N:10](C)[C:11]([NH:20][C:21]([CH3:29])([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH3:22])=[N:12][C:13]=2[C:14]2[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=2)=[CH:4][CH:3]=1.C(N(C(C)C)CC)(C)C.P(Cl)(Cl)([Cl:43])=O>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1>[CH3:22][C:21]([NH:20][C:11]1[N:10]=[C:9]([Cl:43])[C:8]([C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)=[C:13]([C:14]2[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=2)[N:12]=1)([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[CH3:29]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 100 °C
Procedure
5-(4-fluorophenyl)-3-methyl-2-((1-methyl-1-phenylethyl)amino)-6-(4-pyridyl)-(3H)-pyrimidin-4-one (1.24 g, 2.99 mmol), benzyltriethylammonium chloride (2.04 g, 8.97 mmol), and diisopropylethylamine (1.16 g, 1.6 mL 8.97 mmol) were combined in phosphorous oxychloride (ca. 20 mL) and the resulting solution was heated at 100° C. for 16 h. The reaction was cooled to RT, the phosphorous oxychloride was evaporated in vacuo and the residue was partitioned between sat. aq. NaHCO3 and CHCl3. The organic layer was dried over Na2SO4 and then concentrated. The residue was purified by flash chromatography (20% EtOAc:CHCl3) to provide the product as a white solid; MS m/z (M+H)+ 419; C24H20ClFN4 requir. 418.8.
Workup
- temperatureThe reaction was cooled to RT
- customthe phosphorous oxychloride was evaporated in vacuo
- customthe residue was partitioned between sat. aq. NaHCO3 and CHCl3
- dry with materialThe organic layer was dried over Na2SO4
- concentrationconcentrated
- customThe residue was purified by flash chromatography (20% EtOAc:CHCl3)
Sources & evidence
- ORD record
- ord-957cbf07030c4e11adffcc6d80c2358c
- Source dataset
- uspto-grants-2005_07
- Patent number
- US06921762B2
Reaction notes
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