HCID 15229552, compound → HCID 15229684, compound

HRID 1081366Notes

Reaction equation

HRID 1081366 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-8a17b44164a54fadb6c0f1fac6cb7b4a
Source dataset
uspto-grants-1996_12
Patent number
US05585490

Reaction notes

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