HuagongsheHuagongshe Chemistry Print Report · For research reference only
Sodium Carbonate → 4-chloro-7-methyl-5-(naphthalen-2-yl)-7H-pyrrolo[2,3-d]pyrimidine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | (Naphthalen-2-yl)boronic acid | HCID 2734375 | — |
| Reactant | 4-chloro-5-iodo-7-methyl-7H-pyrrolo[2,3-d]pyrimidine | HCID 42609462 | — |
| Catalyst | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | 4-chloro-7-methyl-5-(naphthalen-2-yl)-7H-pyrrolo[2,3-d]pyrimidine | HCID 24905269 | 26.2% |
Reaction Steps
A solution of 4-chloro-5-iodo-7-methyl-7H-pyrrolo[2,3-d]pyrimidine (19 mg, 0.065 mmol), naphthalen-2-yl-2-boronic acid (12.2 mg, 0.071 mmol), Na2CO3 (68.9 mg, 0.65 mmol) and PdCl2(dppf) (26.5 mg, 0.00325 mmol) in THF (3 mL) was heated to reflux overnight under an argon atmosphere. Reaction was concentrated in vacuo and purified by RP-HPLC (MeCN:H2O:0.1% TFA) to yield ZK102 (5 mg, 26% yield). ESI-MS (M+H)+ m/z calcd 294.1, found 294.3.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08642604B2 |
| Source dataset | uspto-grants-2014_02 |
| ORD ID | ord-dfaa7f9fb08240b5acc19bdf0a98b165 |
| Source note | uspto-grants-2014_02 |