HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 884546Generated: October 25, 2026
5-Hydroxyindole → 4-(1H-indol-5-yloxy)-6-methyl-5,8-dihydro-6H-pyrido[3,4-d]pyrimidine-7-carboxylic acid tert-butyl ester
https://huagongshe.com/reaction/884546
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | 5-Hydroxyindole | HCID 16054 | — |
| Reactant | 1,8-Diazabicyclo(5.4.0)undec-7-ene | HCID 81184 | — |
| Reactant | Tert-butyl 4-chloro-6-methyl-5,8-dihydropyrido[3,4-D]pyrimidine-7(6H)-carboxylate | HCID 59394353 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Product | 4-(1H-indol-5-yloxy)-6-methyl-5,8-dihydro-6H-pyrido[3,4-d]pyrimidine-7-carboxylic acid tert-butyl ester | HCID 59394118 | — |
Reaction Steps
A solution of (±)-4-chloro-6-methyl-5,8-dihydro-6H-pyrido[3,4-d]pyrimidine-7-carboxylic acid tert-butyl ester (220 mg, 0.77 mmol), 5-hydroxy indole (155 mg, 1.16 mmol) and MeCN (10 mL) is treated with DBU (0.2 mL, 1.16 mmol) and heated at 80° C. for 4 h. The volume is reduced in vacuo and the residue is separated via FCC (5-90% EtOAc/heptane) to give the title compound. MS (ESI) m/z 381.3 (M+H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08242125B2 |
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| Source dataset | uspto-grants-2012_08 |
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| ORD ID | ord-68db903bfdd543098b81b85bac48d69c |
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| Source note | uspto-grants-2012_08 |
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