Tetrahydrofuran → HCID 58931330, compound

HRID 387778Notes

Reaction equation

HRID 387778 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-cdd38ff7b887421493cff0a38984317d
Source dataset
uspto-grants-2013_02
Patent number
US08372981B2

Reaction notes

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