Aluminium lithium hydride → HCID 59024211, compound

HRID 1678254Notes

Reaction equation

HRID 1678254 reaction equation
C[O:2][C:3]([C:5]1[CH:6]=[CH:7][CH:8]=[C:9]2[C:13]=1[NH:12][C:11]([C:14]1[CH:15]=[C:16]([NH:23][C:24]3[CH:29]=[CH:28][N:27]=[C:26]([NH2:30])[N:25]=3)[CH:17]=[C:18]3[C:22]=1[NH:21][N:20]=[CH:19]3)=[CH:10]2)=O.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[NH2:30][C:26]1[N:25]=[C:24]([NH:23][C:16]2[CH:17]=[C:18]3[C:22](=[C:14]([C:11]4[NH:12][C:13]5[C:9]([CH:10]=4)=[CH:8][CH:7]=[CH:6][C:5]=5[CH2:3][OH:2])[CH:15]=2)[NH:21][N:20]=[CH:19]3)[CH:29]=[CH:28][N:27]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydride2×HCID 59023856HCID 59023856, compound

Product 1

HCID 59024211HCID 59024211, compoundYield 30.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

2-[5-(2-Amino-pyrimidin-4-ylamino)-1H-indazol-7-yl]-1H-indole-7-carboxylic acid methyl ester (Preparation #F.8.1, 0.100 g, 0.000250 mol) was added to a solution of lithium aluminum hydride in tetrahydrofuran (1.0M, 1.0 mL) at about 0° C. in 3 portions. Additional THF (1.0 mL) was added after about 10 min., and after about 40 min, the mixture was allowed to warm to ambient temperature. After about a further 60 min, lithium aluminum hydride in THF (1.0M, 1 mL) was added. About 16 hours later, the mixture was quenched with water and neutralized with a saturated aqueous solution of ammonium chloride. The mixture was diluted with EtOAc, and the layers were separated. The aqueous layer was further extracted with EtOAc, and the combined organics were dried over anhydrous MgSO4 and concentrated to yield {2-[5-(2-amino-pyrimidin-4-ylamino)-1H-indazol-7-yl]-1H-indol-7-yl}-methanol (28 mg, 30% yield); LC/MS Rt (Method e) 0.8 min; m/z (M−H)− 370.5.

Workup

  1. waitAfter about a further 60 min
  2. waitAbout 16 hours later
  3. customthe mixture was quenched with water
  4. additionThe mixture was diluted with EtOAc
  5. customthe layers were separated
  6. extractionThe aqueous layer was further extracted with EtOAc
  7. dry with materialthe combined organics were dried over anhydrous MgSO4
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-29678212b7f642c5a3bcd803bfd20596
Source dataset
uspto-grants-2011_08
Patent number
US08008481B2

Reaction notes

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