Tetrahydrofuran → HCID 58931330, compound

HRID 1433428Notes

Reaction equation

HRID 1433428 reaction equation
O1CCCC1.C([O:8][C:9]([C:11]1[NH:37][C:14]2[N:15]=[CH:16][N:17]=[C:18]([O:19][C:20]3[CH:25]=[CH:24][C:23]([NH:26][C:27]([NH:29][C:30]4[CH:35]=[CH:34][C:33]([F:36])=[CH:32][CH:31]=4)=[O:28])=[CH:22][CH:21]=3)[C:13]=2[CH:12]=1)=O)C.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O>[F:36][C:33]1[CH:34]=[CH:35][C:30]([NH:29][C:27]([NH:26][C:23]2[CH:22]=[CH:21][C:20]([O:19][C:18]3[C:13]4[CH:12]=[C:11]([CH2:9][OH:8])[NH:37][C:14]=4[N:15]=[CH:16][N:17]=3)=[CH:25][CH:24]=2)=[O:28])=[CH:31][CH:32]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 21226445Aluminium lithium hydrideHCID 58930909HCID 58930909, compound

Product 1

HCID 58931330HCID 58931330, compoundYield 70.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

After adding 9 ml of tetrahydrofuran to 55 mg of the 4-{4-[3-(4-fluorophenyl)ureido]phenoxy)-7H-pyrrolo[2,3-d]pyrimidine-6-carboxylic acid ethyl ester synthesized in Example 163 and stirring the mixture, 25 mg of lithium aluminum hydride was added at room temperature and the mixture was stirred for 2 days. Water was then added, liquid separation and extraction were performed with an ethyl acetate-tetrahydrofuran mixed solvent, and the organic layer was filtered with celite and concentrated to dryness to obtain 35 mg of the title compound.

Workup

  1. additionwas added at room temperature
  2. customliquid separation and extraction
  3. filtrationthe organic layer was filtered with celite and
  4. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-ae235c7fddaa4912aeb32a0467874d96
Source dataset
uspto-grants-2009_11
Patent number
US07612092B2

Reaction notes

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