HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1912649Generated: November 1, 2026
1,3-Benzoxazol-6-amine → N-(5-(benzyloxy)-6-p-tolylpyrimidin-4-yl)benzo[d]oxazol-6-amine
https://huagongshe.com/reaction/1912649
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | 1,3-Benzoxazol-6-amine | HCID 584120 | — |
| Reactant | 5-(Benzyloxy)-4-chloro-6-p-tolylpyrimidine | HCID 86665937 | — |
| Reactant | sodium 2-methylpropan-2-olate | HCID 178418730 | — |
| Catalyst | (1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladium | HCID 6505921 | — |
| Solvent | Toluene | HCID 1140 | — |
| Product | N-(5-(benzyloxy)-6-p-tolylpyrimidin-4-yl)benzo[d]oxazol-6-amine | HCID 66958358 | 25.9% |
Reaction Steps
5-(benzyloxy)-4-chloro-6-p-tolylpyrimidine (50 mg, 0.161 mmol) was dissolved in PhMe, to this was added benzo[d]oxazol-6-amine (23.7 mg, 1.1 eq), Pd(dba)2 (4.6 mg, 0.05 eq), t-BuONa (31 mg, 2 eq), and (±)-BINAP (15 mg, 0.15 eq). The mixture was degassed and heated at 115° C. overnight. The mixture was cooled to room temperature, diluted with EtOAc and washed with H2O. Preparative TLC gave 17 mg of the title compound.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08609676B2 |
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| Source dataset | uspto-grants-2013_12 |
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| ORD ID | ord-72bc7667b5d54a25b34032e2f8cef03b |
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| Source note | uspto-grants-2013_12 |
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