Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Pyrimidine | HCID 9260 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | 4-Amino-1-Boc-piperidine | HCID 1268291 | — |
| Reactant | 6-Chloro-N-[4-(methanesulfonyl)phenyl]-5-nitropyrimidin-4-amine | HCID 21897886 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 59856809 | HCID 59856809 | 77.1% |
Reaction Steps
General Procedure for the Addition of Amine to pyrimidine: (6-Chloro-5-nitro-pyrimidin-4-yl)-(4-methanesulfonyl-phenyl)-amine (132 mg, 0.4 mmole), 4-amino-piperidine-1-carboxylic acid tert-butyl ester (0.4 mmole, 1 eq) and K2CO3 (0.4 mmole, 1 eq) were dissolved in DMF, and the mixture was stirred at 60° C. for 1 hour. Final product was precipitated out with water to provide Compound B1 as a yellow solid (152 mg, 77%). 1H NMR (400 MHz CDCl3) δ (ppm): 10.8 (s, 1H), 9.18 (d,1H), 8.17 (s,1H), 7.90 (d,2H), 7.85 (d,2H), 4.39-4.32 (m,1H), 4.02 (m,2H), 3.01 (s,3H), 2.95-2.90 (m, 2H), 2.00 (m,2H), 1.57-1.50 (m,2H), 1.46 (s, 9H). Exact mass calculated for C21H28N6O6S 492.18, LCMS (ESI) m/z 493.4 (M+H+, 100%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07470699B2 |
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| Source dataset | uspto-grants-2008_12 |
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| ORD ID | ord-d3a586fd21cb4f6097276c65f9114b18 |
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| Source note | uspto-grants-2008_12 |
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