Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Sodium Hydroxide | HCID 14798 | — |
| Reactant | N-(2-Amino-4,6-dichloropyrimidin-5-yl)formamide | HCID 10198177 | — |
| Reactant | [(1S,4R)-4-Amino-2-cyclopenten-1-yl]methanol hydrochloride (1:1) | HCID 53471860 | — |
| Solvent | Isobutanol | HCID 6560 | — |
| Product | HCID 9795791 | HCID 9795791 | 74% |
Reaction Steps
2.07 g of N-(2-amino-4,6-dichloro-5-pyrimidinyl)formamide were heated to 80° C. in 40 ml of isobutanol (white suspension). A solution of 1.97 g of (1R,4S)-1-amino-4-hydroxymethyl-2-cyclopentene hydrochloride, 3.8 g of triethylamine and 15 ml of isobutanol was added to the mixture. The mixture was stirred at 80° C. for a further 13 h. 10 ml of 1N NaOH were added to the clear solution at 20° C., followed by evaporation to dryness. The residue underwent flash chromatography (silica gel 60 column, length 8 cm, diameter 6.5 cm, eluent ethyl acetate/methanol 95/5). After evaporating off the eluent and drying the residue, 2.1 g of title compound were obtained. The yield was 74%.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US06137007 |
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| Source dataset | uspto-grants-2000_10 |
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| ORD ID | ord-036df17b63e549ac87a96b68441e306d |
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| Source note | uspto-grants-2000_10 |
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