HuagongsheHuagongshe Chemistry Print Report · For research reference only
Water → {4-[4-(3-Chloro-4-fluoro-phenylamino)-7H-pyrrolo[2,3-d]pyrimidin-6-yl]-phenyl}-methanol
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Sodium Hydroxide | HCID 14798 | — |
| Reactant | Aluminium lithium hydride | HCID 21226445 | — |
| Reactant | 4-[4-(3-Chloro-4-fluoro-phenylamino)-7H-pyrrolo[2,3-d]pyrimidin-6-yl]-benzoic acid ethyl ester | HCID 69179720 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | {4-[4-(3-Chloro-4-fluoro-phenylamino)-7H-pyrrolo[2,3-d]pyrimidin-6-yl]-phenyl}-methanol | HCID 11234001 | — |
Reaction Steps
570 mg (15 mmol) lithium aluminium hydride are suspended in 150 ml dry THF at RT. 4-[4-(3-Chloro-4-fluoro-phenylamino)-7H-pyrrolo[2,3-d]pyrimidin-6-yl]-benzoic acid ethyl ester (1.23 g, 3 mmol) are added and the resulting mixture is heated to reflux for 1 h. The mixture is cooled in an ice bath and treated sequentially with water (0.57 ml), 15% sodium hydroxide solution (0.57 ml) and water (1.71 ml). The solid aluminum complex is removed by filtration (Hyflo Super Cel®; Fluka, Buchs, Switzerland), the filtrate dried over sodium sulfate and the solvent evaporated. The residue was suspended in water, filtered and dried to give the title compound; m.p.>300° C.; HPLC tR=9.14 min.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07390805B2 |
| Source dataset | uspto-grants-2008_06 |
| ORD ID | ord-278930d98fae442dbae2f0eeb80f31ce |
| Source note | uspto-grants-2008_06 |