Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | Benzophenone imine | HCID 136809 | — |
| Reactant | 2-Chloro-7-cyclopentyl-N,N-dimethyl-7H-pyrrolo[2,3-d]pyrimidine-6-carboxamide | HCID 58315432 | — |
| Catalyst | palladium(II) acetate | HCID 167845 | — |
| Catalyst | Binap, (A+-)- | HCID 634876 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | HCID 86686649 | HCID 86686649 | 80% |
Reaction Steps
To a suspension of 2-chloro-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidine-6-carboxylic acid dimethylamide (2.93 g, 10 mmol) in 50 mL Dioxane were added benzophenone imine (1.90 g, 10.5 mmol), Pd(OAc)2 (0.11 g, 0.5 mmol), BINAP (0.31 g, 0.5 mmol) and Cs2CO3 (4.89 g, 15 mmol) and the flask was purged with N2. Then the tube was sealed and the mixture was heated for 1 h at 120° C. Then the suspension was added with heptane and filtered. The precipitate was extracted with DCM and the extract was purified by SiO2 column chromatography to give 2-(benzhydrylidene-amino)-7-(1-ethyl-butyl)-7H-pyrrolo[2,3-d]pyrimidine-6-carboxylic acid dimethylamide (3.5 g, 8.0 mmol, 80% yield). MS m/z 438.5 (M+H)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08957074B2 |
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| Source dataset | uspto-grants-2015_02 |
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| ORD ID | ord-7d1cb9458e2d42859b2abe13e5f0e9cb |
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| Source note | uspto-grants-2015_02 |
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