Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Diethyl cyanophosphonate | HCID 76257 | — |
| Reactant | 4-Chloro-o-anisic acid | HCID 93682 | — |
| Reactant | HCID 67176912 | HCID 67176912 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 44540011 | HCID 44540011 | 57.5% |
Reaction Steps
To a solution of 0.067 g (0.20 mmol) of 9-aminomethyl-2-pyrimidin-4-yl-6,7,8,9-tetrahydro-pyrido[1,2-a]pyrimidin-4-one hydrobromide (1:1) dissolved in 2.00 mL of dimethylformamide were added 0.053 g (0.20 mmol) of 4-chloro-2-methoxy-benzoic acid, 0.030 mL (0.20 mmol) of diethylcyanophosphonate and 0.140 mL (1.00 mmol) of triethylamine. The resulting mixture was stirred at room temperature for 2 hours. Water and ethyl acetate were added, the mixture was extracted with ethyl acetate and the organic phase was washed with a saturated solution of ammonium chloride, dried over sodium sulfate and concentrated. A purification on silica gel (eluant: dichloromethane with 5% of methanol) gave 0.049 g (57%) of pure product obtained in the form of free base as a solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08614219B2 |
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| Source dataset | uspto-grants-2013_12 |
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| ORD ID | ord-7f7b12b6aec645bd8080992a9c2b8963 |
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| Source note | uspto-grants-2013_12 |
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