Water → {4-[4-(3-Chloro-4-fluoro-phenylamino)-7H-pyrrolo[2,3-d]pyrimidin-6-yl]-phenyl}-methanol

HRID 133021Notes

Reaction equation

HRID 133021 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C([O:9][C:10](=O)[C:11]1[CH:16]=[CH:15][C:14]([C:17]2[NH:34][C:20]3[N:21]=[CH:22][N:23]=[C:24]([NH:25][C:26]4[CH:31]=[CH:30][C:29]([F:32])=[C:28]([Cl:33])[CH:27]=4)[C:19]=3[CH:18]=2)=[CH:13][CH:12]=1)C.O.[OH-].[Na+]>C1COCC1>[Cl:33][C:28]1[CH:27]=[C:26]([NH:25][C:24]2[C:19]3[CH:18]=[C:17]([C:14]4[CH:15]=[CH:16][C:11]([CH2:10][OH:9])=[CH:12][CH:13]=4)[NH:34][C:20]=3[N:21]=[CH:22][N:23]=2)[CH:31]=[CH:30][C:29]=1[F:32]

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 691797204-[4-(3-Chloro-4-fluoro-phenylamino)-7H-pyrrolo[2,3-d]pyrimidin-6-yl]-benzoic acid ethyl ester

Product 1

HCID 11234001{4-[4-(3-Chloro-4-fluoro-phenylamino)-7H-pyrrolo[2,3-d]pyrimidin-6-yl]-phenyl}-methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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.

Workup

  1. temperaturethe resulting mixture is heated
  2. temperatureto reflux for 1 h
  3. temperatureThe mixture is cooled in an ice bath
  4. customThe solid aluminum complex is removed by filtration (Hyflo Super Cel®; Fluka, Buchs, Switzerland)
  5. dry with materialthe filtrate dried over sodium sulfate
  6. customthe solvent evaporated
  7. filtrationfiltered
  8. customdried

Sources & evidence

ORD record
ord-278930d98fae442dbae2f0eeb80f31ce
Source dataset
uspto-grants-2008_06
Patent number
US07390805B2

Reaction notes

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