Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Formic Acid | HCID 284 | — |
| Reactant | Acetic Anhydride | HCID 7918 | — |
| Reactant | methyl (2-aminopyrimidinyl)acetate | HCID 11286676 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 13060169 | HCID 13060169 | 69.8% |
Reaction Steps
A mixture of acetic anhydride (32.7 g.) and formic acid (16.2 g.) was stirred at 50° to 60° C. for 30 minutes. The solution was added to a suspension of methyl 2-(2-aminopyrimidin-4-yl)acetate (17.93 g.) in ethyl acetate (300 ml.) at room temperature over 10 minutes, and the solution was stirred at room temperature for 3 hours. After removing the insoluble substance by filtration, water (300 ml.) was added to the filtrate, and then the mixture was adjusted to pH 7 with sodium bicarbonate. The aqueous layer was separated and extracted with ethyl acetate. The extract and the organic layer were combined, washed with a saturated aqueous solution of sodium chloride, dried over magnesium sulfate, treated with activated charcoal, and then concentrated under reduced pressure. The residue was triturated with diethyl ether to give methyl 2-(2-formamidopyrimidin-4-yl)acetate (14.62 g.), mp 103° to 107° C.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US04395411 |
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| Source dataset | uspto-grants-1983_07 |
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| ORD ID | ord-b270313f692f46498311a15d0adeafb3 |
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| Source note | uspto-grants-1983_07 |
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