Synthesis of 6-(alkoxymethyl)- and 6-(alkylsulfanylmethyl)furo[2,3-<i>d</i>]pyrimidin-2(3<i>H</i>)-one analogues
Why this work is in the frame
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Bibliographic record
Abstract
Treatment of 6-(hydroxymethyl)furo[2,3-d]pyrimidin-2(3H)-one (2) with 1-iodoalkanes and potassium carbonate resulted in predominant formation of N3 (and minor amounts of O2) alkylated regioisomers. Treatment of the 3-alkyl products (3) with thionyl chloride gave highly reactive 6-chloromethyl intermediates (5). Direct solvolysis of 5 in alcohol solutions (~50 °C) produced 3-alkyl-6-(alkoxymethyl)furopyrimidin-2(3H)-ones (6), whereas extensive decomposition of 5 occurred with added base promoters. Sonication of 5 with sodium thioacetate in acetonitrile gave the air-stable 6-(alkylsulfanylmethyl) intermediates (7), which were subjected to deacetylation (methanolic sodium methoxide) and in situ alkylation to give 3-alkyl-6-(alkylsulfanylmethyl)furo[2,3-d]pyrimidin-2(3H)-ones (8). Lipophilic derivatives of furo[2,3-d]pyrimidin-2(3H)-one are of interest as potential inhibitors of viral penetration of cells.Key words: furo[2,3-d]pyrimidin-2(3H)-ones, alkyl, ether and thioether derivatives of furo[2,3-d]pyrimidin-2(3H)-one.
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Full frame distilled prediction
Teacher imitationNot calibrated prevalence, not ground truth. Human validation pending. Learned from the 10,348 direct Codex labels and 10,348 direct Gemma labels. Candidate is the union of thresholded teacher heads; consensus is their intersection. These outputs are machine_predicted_unvalidated and are not human labels or direct frontier model labels.
Codex and Gemma teacher scores by category
| Category | Codex | Gemma |
|---|---|---|
| Metaresearch | 0.001 | 0.001 |
| Meta-epidemiology (narrow) | 0.000 | 0.000 |
| Meta-epidemiology (broad) | 0.001 | 0.000 |
| Bibliometrics | 0.000 | 0.000 |
| Science and technology studies | 0.000 | 0.000 |
| Scholarly communication | 0.000 | 0.000 |
| Open science | 0.000 | 0.000 |
| Research integrity | 0.000 | 0.000 |
| Insufficient payload (model declined to judge) | 0.001 | 0.000 |
Machine scores (provisional)
The two teacher heads of the student model, read on this work. A score orders the frame for review; it never asserts a category, and the validation status ships verbatim with every row.
Baseline scores from an immature model (maturity gate not passed, 7 training rounds). Scores rank; they never assert a category.
score_only:v0-immature-baseline · verbatim from the scoring run: score_only means the number may rank works, and no category label ships from it