HCID 15229552, compound → HCID 15229684, compound

HRID 1586964Notes

Reaction equation

HRID 1586964 reaction equation
[C:1]1([C:7]2[N:8]=[CH:9][C:10]3[NH:19][C:18]4[CH2:17][CH2:16][C:15](=[O:20])[CH2:14][C:13]=4[C:11]=3[N:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[OH:20][CH:15]1[CH2:16][CH2:17][C:18]2[NH:19][C:10]3[CH:9]=[N:8][C:7]([C:1]4[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=4)=[N:12][C:11]=3[C:13]=2[CH2:14]1

Participants

4

Reactant 2

HCID 15229552HCID 15229552, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 15229684HCID 15229684, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 2-Phenyl-5,6,7,9-tetrahydro-8H-indolo[3,2-d]-pyrimidin-8-one (200 mg) and dry tetrahydrofuran (5 mL) was added lithium aluminum hydride (100 mg) in one portion. After 1 h at room temperature the reaction was quenched with 1N NaOH, the reaction was filtered through celite and the solvent was removed in vacuo and the residue was subjected to flash chromatography on silica gel with 10% methanol in methylene chloride as the eluent to afford 8-Hydroxy-2-phenyl-6,7,8,9-tetrahydro-5H-indolo[3,2-d]-pyrimidine (Compound 31) melting at 211°-212° C.

Workup

  1. customAfter 1 h at room temperature the reaction was quenched with 1N NaOH
  2. filtrationthe reaction was filtered through celite
  3. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-e8124785405d440bb786f6c7addfb792
Source dataset
uspto-grants-1993_06
Patent number
US05216159

Reaction notes

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