Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Cyclopropylamine | HCID 69828 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | 2,4-Dichloro-5-fluoropyrimidine | HCID 250705 | — |
| Reactant | 3-Morpholinecarboxylic acid | HCID 3340152 | — |
| Reactant | Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) | HCID 9886157 | — |
| Solvent | Dimethyl Sulfoxide | HCID 679 | — |
| Solvent | Water | HCID 962 | — |
| Product | HCID 83103480 | HCID 83103480 | 21.62% |
Reaction Steps
A round-bottomed flask equipped with a magnetic stirrer was added 2,4-dichloro-5-fluoropyrimidine (0.835 g, 5 mmol), DMSO (1 ml), morpholine-3-carboxylic acid (0.656 g, 5.00 mmol) and DIPEA (3.49 ml, 20.00 mmol). The reaction was stirred at 80° C. for 10 minutes then cooled to ambient temperature, HATU (2.85 g, 7.50 mmol) was added followed by cyclopropanamine (0.526 ml, 7.50 mmol) and the reaction mixture was again heated at 80° C. for 2 hours. Upon completion the reaction was suspended in water and filtered. The collected solid was washed successively with water, small amount of ethanol and diethyl ether. The solid was dried in vacuo for 16 hours to afford 4-(2-chloro-5-fluoropyrimidin-4-yl)-N-cyclopropylmorpholine-3-carboxamide (0.325 g, 1.081 mmol, 21.62% yield) as a white solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08163755B2 |
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| Source dataset | uspto-grants-2012_04 |
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| ORD ID | ord-3fccab769114462ead872bd50610d0bb |
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| Source note | uspto-grants-2012_04 |
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