Buchwald–Hartwig amination: (2-Chloro-6-methylpyridin-4-yl)methanol → (4-Hydroxymethyl-6-methyl-pyridine-2-yl)-carbamic acid tert-butyl ester
0% yield, run at 80 °C, as recorded by experimental reaction archive. The written procedure is below.
The atoms, from reactants to products
What was in the flask
| Role | Species | Formula | Yield |
|---|---|---|---|
| Reactant | (2-Chloro-6-methylpyridin-4-yl)methanol | C₇H₈ClNO | |
| Reactant | tert-Butyl carbamate | C₅H₁₁NO₂ | |
| Reagent | Cesium carbonate | CCs₂O₃ | |
| Catalyst | 1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) | C₃₉H₃₂OP₂ | |
| Catalyst | Bis(dibenzylideneacetone)palladium | C₅₁H₄₂O₃Pd₂ | |
| Solvent | 1,4-Dioxane | C₄H₈O₂ | |
| Product | (4-Hydroxymethyl-6-methyl-pyridine-2-yl)-carbamic acid tert-butyl ester | C₁₂H₁₈N₂O₃ | 0% |
Conditions
- Temperature
- 80 °C
Yield
- 0% of (4-Hydroxymethyl-6-methyl-pyridine-2-yl)-carbamic acid tert-butyl ester.
Other recorded runs with the same starting material
No other run in the library makes this product. These runs of the same class start from one of the same reactants, which is the nearest company this record has.
- tert-butyl N-(5-chloropyridazin-3-yl)carbamate100%
- tert-butyl N-(3-fluoro-4-formylphenyl)carbamate97%
- tert-butyl N-(3-fluoro-5-methyl-2-pyridinyl)carbamate26%
- 2-(Tert-butoxycarbonylamino)-6-chloroisonicotinic acid0%
- N-[5-amino-4-methoxy-2-(4-methyl-1-piperazinyl)phenyl]carbamic acid 1,1-dimethylethyl ester0%
- tert-Butyl (5-fluoro-6-methylpyridin-2-yl)carbamate0%
- 3-(Boc-amino)pyridinenot recorded
- tert-butyl N-(3-fluoro-5-methyl-2-pyridinyl)carbamate26%
- 3-(Boc-amino)pyridinenot recorded
- 3-(Boc-amino)pyridinenot recorded
- 3-(Boc-amino)pyridinenot recorded
- 3-(Boc-amino)pyridinenot recorded
Procedure
Copied from the source record, unedited
A 2.0-5.0 mL microwave vial was charged with XANTPHOS (14.66 mg, 0.03 mmol), Pd2(dba)3 (29.1 mg, 0.03 mmol), CESIUM CARBONATE (155 mg, 0.48 mmol),(2-chloro-6-methylpyridin-4-yl)methanol (50 mg, 0.32 mmol), tert-butyl carbamate (44.6 mg, 0.38 mmol) and dioxane (3 mL). The reaction mixture was degassed for 2 minutes with nitrogen, and then the reaction mixture was stirred at 80°C under microwave irradiation for 30 min. Water (5 mL) was added and the mixture was washed using EtOAc (3 x 10 mL). The organic layers were combined, dried using MgSO4, filtered and concentrated. The crude material was loaded on a 12g silica gel column and purified on a Teledyne Isco instrument, eluting with 0% to 20% EtOAc in DCM. The product that seems to be the compound was collected. Unfrtunately NMR showed that
The source
This record comes from experimental reaction archive (ord-4ba8493a4d7f4107b8a89b01cdd11168). Open the source and check it against what is on this page.
experimental reaction archive record ord-4ba8493a4d7f4107b8a89b01cdd11168 from dataset "750 AstraZeneca ELN dataset" (url: https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471). No atom mapping is provided by the source.
How to read this record
This is one experiment, not a rule. It says that on one occasion these species were combined under these conditions and this came out. It does not say the reaction will give the same result on your substrate, and nothing on the page has been generalised into a claim that it would.
The pathway is a separate question, kept on separate pages. A mechanism here is the canonical arrow pushing for a class, run on real structures and labelled rule-derived. It is not evidence, and this record is not a mechanism.
Where to next
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