Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Pentanoic Acid | HCID 7991 | — |
| Reactant | Dicyclohexylcarbodiimide | HCID 10868 | — |
| Reactant | 4-Pyrrolidinopyridine | HCID 75567 | — |
| Reactant | HCID 19734917 | HCID 19734917 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 15027169 | HCID 15027169 | 76.8% |
Reaction Steps
In a 200 ml-round bottom flask, 2.00 g (5.81 mM) of 2-undecyl-5-(3-fluoro-4-hydroxyphenyl)pyrimidine, 0.60 g (5.87 mM) of valeric acid and 50 ml of dichloromethane were placed and dissolved. To the solution, 1.21 g (5.86 mM) of N,N'-dicyclohexylcarbodiimide and 0.10 g of 4-pyrrolidinopyridine were successively added under stirring at room temperature, followed by further stirring for 4 hours and 45 minutes at room temperature. After stirring, the mixture was left standing at room temperature to precipitate N,N'-dicyclohexylurea. The resultant, N,N'-dichclohexylurea was filtered off and the solvent of the filtrate was distilled-off under reduced pressure. The residue was purified by silica gel column chromatography (eluent: toluene/ethyl acetate=100/1) and recrystallized two times from a minute solvent of acetone-methanol to obtain 1.91 g of 2-undecyl-5-(3-fluoro-4-pentanoyloxyphenyl)pyrimidine (Yield: 76.8). ##STR28##
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US05269964 |
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| Source dataset | uspto-grants-1993_12 |
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| ORD ID | ord-e8f9c3913b0a4585bdb36b2da2029345 |
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| Source note | uspto-grants-1993_12 |
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