HuagongsheHuagongshe Chemistry Print Report · For research reference only
5-Hydroxyindole → (+/-)-4-(1H-Indol-5-yloxy)-8-methyl-5,8-dihydro-6H-pyrido[3,4-d]pyrimidine-7-carboxylic acid tert-butyl ester
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-8-methyl-5,8-dihydropyrido[3,4-d]pyrimidine-7(6H)-carboxylate | HCID 59394669 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Product | (+/-)-4-(1H-Indol-5-yloxy)-8-methyl-5,8-dihydro-6H-pyrido[3,4-d]pyrimidine-7-carboxylic acid tert-butyl ester | HCID 59394465 | — |
Reaction Conditions
| Temperature | 80 °C |
|---|
Reaction Steps
To a solution of 4-chloro-8-methyl-5,8-dihydro-6H-pyrido[3,4-d]pyrimidine-7-carboxylic acid tert-butyl ester (228 mg, 0.80 mmol), 5-hydroxyindole (139 mg, 1.05 mmol) and MeCN (5 mL) is added DBU (0.15 mL, 1.05 mmol). The resulting misture is heated at 80° C. for 4 h. The reaction is then concentrated in vacuo and the residue separated via FCC (5-60% EtOAc/heptane). MS (ESI) m/z 381.1 (M+H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08541432B2 |
| Source dataset | uspto-grants-2013_09 |
| ORD ID | ord-d00b4fc61fe247708747fde4069fb94b |
| Source note | uspto-grants-2013_09 |