Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Bicarbonate Ion | HCID 769 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | 6-(Bromomethyl)-2-imino-2,3-dihydropteridin-4-amine--hydrogen bromide (1/1) | HCID 12503242 | — |
| Reactant | HCID 24212136 | HCID 24212136 | — |
| Solvent | Dimethylacetamide | HCID 31374 | — |
| Product | HCID 58847317 | HCID 58847317 | 41% |
Reaction Steps
To a solution of 6-bromomethyl-2,4-pteridinediamine hydrobromide (53.7 mg, 0.1598 mmol) in anhydrous N,N dimethylacetamide was added 2-amino-3-(4-tert-butoxy-phenyl)-propionic acid tert-butyl ester hydrochloride (51.58 mg, 0.1758 m mol). Under positive pressure of Argon, iPr2EtN (33.69 ul) was added. The reaction mixture was stirred at 50° C. for 4 hrs and then at room temperature overnight. The crude product was poured into saturated bicarbonate solution. The resulted precipitate was collected and purified by preparative HPLC. 27.6 mg product was obtained. Yield: 41%; 1H NMR (500 MHz, DMSO-d6): δ 1.22491(s, 9H), 1.26835 (s, 9H), 2.921–2.971 (m, 2H), 4.130 (b, 1H), 4.427(s, 2H), 6.91485–6.93165(d, J=8.4 Hz, 2H), 7.16037–7.17723(d, J=8.43 Hz, 2H), 8.89353 (s, 1H); 9.13119 (s, 2H), 9.30829 (s, 2H); ESI-MS: m/z 468 (M++1)
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07208493B2 |
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| Source dataset | uspto-grants-2007_04 |
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| ORD ID | ord-d65f1572ffc54186a7aaba7eba7ac355 |
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| Source note | uspto-grants-2007_04 |
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