HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1918927Generated: October 27, 2026
1,2-Dimethoxyethane → HCID 68096416, compound
https://huagongshe.com/reaction/1918927
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | 1,2-Dimethoxyethane | HCID 8071 | — |
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | 1-methyl-3-(pyrimidin-4-ylamino)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2(1H)-one | HCID 58043862 | — |
| Reactant | 2-Bromo-6-[7,7-dimethyl-1-oxo-3,4,7,8-tetrahydro-1H-cyclopenta[4,5]pyrrolo[1,2-a]pyrazin-2(6H)-yl]benzyl Acetate | HCID 68096885 | — |
| Catalyst | HCID 178418397 | HCID 178418397 | — |
| Solvent | Methanol | HCID 887 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Diethyl Ether | HCID 3283 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 68096416 | HCID 68096416 | 56.1% |
Reaction Steps
A microwave tube equipped with a magnetic stirrer was charged with 1-methyl-3-(pyrimidin-4-ylamino)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2(1H)-one 109c (210 mg, 0.64 mmol), 167f (140 mg, 0.3 mmol), 1,2-dimethoxyethane (4 mL) and 1M aqueous sodium carbonate (1 mL). After bubbling N2 for 15 min, Pd(PPh3)4 (18 mg, 0.02 mmol) was added. The mixture was heated in microwave to 130° C. for 25 min. After this time, ethyl acetate (5 mL) and water (5 mL) were added. The separated aqueous layer was extracted with ethyl acetate (2×5 mL). The combined organics were washed with brine (10 mL), dried over sodium sulfate, filtered and concentrated under reduced pressure. The resulting residue was purified by column chromatography eluting with a gradient of CH2Cl2-60:35:5 CH2Cl2:diethyl ether:methanol to afford a 53% yield (93 mg) of 167g.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08618107B2 |
|---|
| Source dataset | uspto-grants-2013_12 |
|---|
| ORD ID | ord-ff964e80d2f94b06beb966f1a32877a3 |
|---|
| Source note | uspto-grants-2013_12 |
|---|
