Diisobutylaluminumhydride → HCID 25206018, compound

HRID 1809174Notes

Reaction equation

HRID 1809174 reaction equation
[H-].C([Al+]CC(C)C)C(C)C.C[O:12][C:13](=O)[C:14]1[CH:19]=[CH:18][C:17]([CH2:20][NH:21][C:22]2[C:23]3[N:24]([C:28]([C:31]4[CH:36]=[CH:35][C:34]([O:37][CH3:38])=[C:33]([O:39][CH3:40])[CH:32]=4)=[CH:29][N:30]=3)[CH:25]=[CH:26][N:27]=2)=[CH:16][CH:15]=1>ClCCl>[CH3:40][O:39][C:33]1[CH:32]=[C:31]([C:28]2[N:24]3[CH:25]=[CH:26][N:27]=[C:22]([NH:21][CH2:20][C:17]4[CH:16]=[CH:15][C:14]([CH2:13][OH:12])=[CH:19][CH:18]=4)[C:23]3=[N:30][CH:29]=2)[CH:36]=[CH:35][C:34]=1[O:37][CH3:38]

Participants

4

Reactant 2

HCID 21225700DiisobutylaluminumhydrideHCID 25206651HCID 25206651, compound

Product 1

HCID 25206018HCID 25206018, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Diisobutylaluminium hydride (1 ml, 1.0 mmol, 1 M solution in dichloromethane) was added dropwise to a solution of 4-{[3-(3,4-dimethoxy-phenyl)-imidazo[1,2-a]pyrazin-8-ylamino]-methyl}-benzoic acid methyl ester (0.10 g, 0.24 mmol) in dichloromethane (1 mL) at ambient temperature. The reaction mixture was stirred for 1 hour then diluted with dichloromethane (50 ml) and washed with 1 M aqueous potassium sodium tartarate solution (30 mL) and water (30 mL). The organic layer was dried with magnesium sulphate, filtered and concentrated in vaccuo. The crude material was purified by column chromatography using 1:1 dichloromethane:ethyl acetate as eluent. The product, (4-{[3-(3,4-Dimethoxy-phenyl)-imidazo[1,2-a]pyrazin-8-ylamino]-methyl}-phenyl)-methanol, is obtained as a white solid (35 mg, 37%) (LC-MS m/z 391 [M+H]+).

Workup

  1. washwashed with 1 M aqueous potassium sodium tartarate solution (30 mL) and water (30 mL)
  2. dry with materialThe organic layer was dried with magnesium sulphate
  3. filtrationfiltered
  4. concentrationconcentrated in vaccuo
  5. customThe crude material was purified by column chromatography

Sources & evidence

ORD record
ord-366054a8820c42e69b06aa72258c0c0d
Source dataset
uspto-grants-2013_01
Patent number
US08362018B2

Reaction notes

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