Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ammonium Chloride | HCID 25517 | — |
| Reactant | 4-Amino-2-(methylsulfanyl)pyrimidine-5-carbaldehyde | HCID 295769 | — |
| Reactant | Triethyl 2-fluoro-2-phosphonoacetate | HCID 2734865 | — |
| Reactant | Butyllithium | HCID 178418339 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 22134704 | HCID 22134704 | 92.1% |
Reaction Steps
A solution of 1.74 g (10.33 mmol) of (diethoxy-phosphoryl)-fluoro-acetic acid ethyl ester in 20 mL of tetrahydrofuran is cooled to −78° C. and treated dropwise with 12.9 mL (20.65 mmol) of a 1.6 M solution of n-butyl lithium in hexanes. After stirring for 30 minutes at −78° C. the solution is treated with 1.74 g (10.33 mmol) of 4-amino-2-methylsulfanyl-pyrimidine-5-carboxaldehyde (Example 3), allowed to warm to room temperature, and stirred overnight. The reaction is treated with saturated aqueous ammonium chloride, then water. The solid is collected by filtration and washed with diethyl ether to give 2.01 g (92%) of the product.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07053070B2 |
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| Source dataset | uspto-grants-2006_05 |
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| ORD ID | ord-f8d6334e0b38473c986f4db3a5b14f57 |
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| Source note | uspto-grants-2006_05 |
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