HuagongsheHuagongshe Chemistry Print Report · For research reference only
Bis(trimethylsilyl)carbodiimide → HCID 58980958, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Bis(trimethylsilyl)carbodiimide | HCID 70473 | — |
| Reactant | 5-chloro-1H-indole-3-carbaldehyde | HCID 2795374 | — |
| Reactant | 4-Acetyl-1-methyl-1H-pyrrole-2-carbaldehyde | HCID 12676268 | — |
| Reactant | 6-hydrazino-1-isobutyl-3-methyl-2,4(1H,3H)-pyrimidinedione | HCID 19356084 | — |
| Reactant | 3-(4-acetyl-1-methyl-1H-pyrrol-2-yl)-2-[(5-chloro-1H-indol-3-yl)methyl]-7-isobutyl-5-methyl-2H-pyrazolo[3,4-d]pyrimidine-4,6(5H,7H)-dione | HCID 58981140 | — |
| Catalyst | Titanium Tetrachloride | HCID 24193 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 58980958 | HCID 58980958 | — |
Reaction Steps
This compound was made in two steps following the procedure described above, starting with 6-hydrazino-1-isobutyl-3-methylpyrimidine-2,4(1H,3H)-dione, and condensing first 5-chloro-1H-indole-3-carbaldehyde, followed by 4-acetyl-1-methyl-1H-pyrrole-2-carbaldehyde. The isolated 3-(4-acetyl-1-methyl-1H-pyrrol-2-yl)-2-[(5-chloro-1H-indol-3-yl)methyl]-7-isobutyl-5-methyl-2H-pyrazolo[3,4-d]pyrimidine-4,6(5H,7H)-dione was treated with a cold solution of bis(trimethylsilyl)carbodiimide and TiCl4 at 0° C. in anhydrous dichloromethane. The mixture was stirred at room temperature for 4 h. The crude reaction product was purified by semi-prep RPHPLC eluting with water/acetonitrile/trifluoroacetic acid mixtures. 531.2 (M+H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07285558B2 |
| Source dataset | uspto-grants-2007_10 |
| ORD ID | ord-8f1b9733a04f4c7b8720531dbf7cfb38 |
| Source note | uspto-grants-2007_10 |