HuagongsheHuagongshe Chemistry Print Report · For research reference only
Sodium hydride → 4-(5-(Benzyloxy)-6-p-tolylpyrimidin-4-ylamino)-2-fluorobenzonitrile
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | 4-Amino-2-fluorobenzonitrile | HCID 2783413 | — |
| Reactant | 5-(Benzyloxy)-4-chloro-6-p-tolylpyrimidine | HCID 86665937 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | 4-(5-(Benzyloxy)-6-p-tolylpyrimidin-4-ylamino)-2-fluorobenzonitrile | HCID 66958357 | 76.1% |
Reaction Steps
The compound from step 4 (0.3 g, 0.96 mmol) was dissolved in DMF (4.83 ml), 4-cyano-3-fluoroaniline (0.131 g, 1 eq) and NaH (0.155 g of 60% dispersion in mineral oil, 4 eq) were added. After 1 hour LCMS showed complete conversion, the reaction was quenched with NH4Cl(sat) and extracted with EtOAc. The extracts were dried concentrated and the residue purified by silica gel chromatography (0-20% EtOAc in hexane) to give 0.3 g of the title compound.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08609676B2 |
| Source dataset | uspto-grants-2013_12 |
| ORD ID | ord-3ac2c0115ee04a3dbd1dc7652f949ebd |
| Source note | uspto-grants-2013_12 |