Aluminium lithium hydride → HCID 11293122, compound

HRID 2373894Notes

Reaction equation

HRID 2373894 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([C:15]2[N:16]=[C:17]([C:25]3[CH:26]=[C:27]([CH2:31][OH:32])[CH:28]=[CH:29][CH:30]=3)[N:18]3[CH:23]=[CH:22][N:21]=[C:20](Cl)[C:19]=23)[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.COC(=O)C1C=CC=C(C2N3C=CN=C(Cl)C3=C(C3C=CC=C(OCC4C=CC=CC=4)C=3)[N:43]=2)C=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[NH2:43][C:20]1[C:19]2[N:18]([C:17]([C:25]3[CH:26]=[C:27]([CH2:31][OH:32])[CH:28]=[CH:29][CH:30]=3)=[N:16][C:15]=2[C:11]2[CH:12]=[CH:13][CH:14]=[C:9]([O:8][CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[CH:10]=2)[CH:23]=[CH:22][N:21]=1

Participants

5

Reactant 3

HCID 21226445Aluminium lithium hydrideHCID 59852731HCID 59852731, compoundHCID 59852782HCID 59852782, compound

Product 1

HCID 11293122HCID 11293122, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

{3-[1-(3-Benzyloxyphenyl)-8-chloroimidazo[1,5-a]pyrazin-3-yl]-phenyl}-methanol: To a solution of 3-[1-(3-benzyloxyphenyl)-8-chloroimidazo[1,5-a]pyrazin-3-yl]-benzoic acid methyl ester (552 mg, 1.17 mmol) in THF (25 mL), cooled to 0° C., 1M LiAlH4 (880 μL, 797 mg, 0.880 mmol) was added, under N2, and the reaction solution was vortexed for 2 h. Upon addition, the reaction mixture changed from yellow to dark green in color. The reaction was quenched with potassium sodium tartrate sat. aq. sol. (25 mL), extracted with EtOAc (3×20 mL), washed with brine (1×40 mL), dried over MgSO4, and filtered. The crude material was purified by filtration through a plug of silica gel plug [eluting with EtOAc:CH2Cl2 1:1 (400 mL)] and concentrated, affording 366.3 mg (71%, 0.829 mmol) of the title compound, as a yellow solid; 1H NMR (CDCl3, 400 MHz) δ 4.82 (d, J=6.0 Hz, 2H), 5.15 (s, 2H), 7.05-7.11 (m, 1H), 7.32-7.43 (m, 7H), 7.44-7.49 (m, 2H), 7.52-7.61 (m, 2H), 7.73-7.78 (m, 1H), 7.87 (s, 1H), 8.05 (d, J=4.8 Hz, 1H); MS (ES+): m/z 441.9/443.9 (100/38) [MH+].

Workup

  1. additionUpon addition
  2. customThe reaction was quenched with potassium sodium tartrate sat. aq. sol. (25 mL)
  3. extractionextracted with EtOAc (3×20 mL)
  4. washwashed with brine (1×40 mL)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. filtrationThe crude material was purified by filtration through a plug of silica gel plug [eluting with EtOAc:CH2Cl2 1:1 (400 mL)]
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-0acb82f183eb42f4b0440e3f3ece2c4a
Source dataset
uspto-grants-2008_12
Patent number
US07459554B2

Reaction notes

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