Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | N-tert-butyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiophene-2-sulfonamide | HCID 57468817 | — |
| Reactant | HCID 58169276 | HCID 58169276 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | HCID 66927369 | HCID 66927369 | 23.3% |
Reaction Steps
A mixture of 2-bromo-N-(5-tert-butyl-1H-pyrazol-3-yl)-5-chloropyrimidin-4-amine (250 mg, 0.87 mmol), PdCl2(dppf)CH2Cl2 (106 mg, 0.13 mmol, 0.15 eq), N-tert-butyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiophene-2-sulfonamide (336 mg, 1.13 mmol, 1.3 eq), Na2CO3 (323 mg, 3.18 mmol, 3.5 equiv.) in dioxane was heated at 95° C. for 2 h under N. The reaction mixture was cooled to room temperature, and extracted with THF. The combined layers were concentrated and purified by silica gel chromatography (EA/PE 1:2) to afford N-tert-butyl-5-(4-(5-tert-butyl-1H-pyrazol-3-ylamino)-5-chloropyrimidin-2-yl)thiophene-2-sulfonamide (95 mg, 21%). LC-MS (m/z)=427 [M+H]+
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09422271B2 |
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| Source dataset | uspto-grants-2016_08 |
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| ORD ID | ord-1726a8683a9d4b5788fbb45cd1a7f129 |
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| Source note | uspto-grants-2016_08 |
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