Aluminium lithium hydride → HCID 90402667, compound

HRID 2200719Notes

Reaction equation

HRID 2200719 reaction equation
[Cl:1][C:2]1[CH:39]=[CH:38][C:5]([CH2:6][N:7]2[C:15]3[C:14](=[O:16])[N:13]([CH:17]4[CH2:20][CH:19]([C:21]([O-])=[O:22])[CH2:18]4)[C:12](=[O:24])[N:11]([CH3:25])[C:10]=3[N:9]=[C:8]2[O:26][C:27]2[CH:32]=[CH:31][CH:30]=[C:29]([O:33][C:34]([F:37])([F:36])[F:35])[CH:28]=2)=[CH:4][CH:3]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]2[C:15]3[C:14](=[O:16])[N:13]([CH:17]4[CH2:18][CH:19]([CH2:21][OH:22])[CH2:20]4)[C:12](=[O:24])[N:11]([CH3:25])[C:10]=3[N:9]=[C:8]2[O:26][C:27]2[CH:32]=[CH:31][CH:30]=[C:29]([O:33][C:34]([F:37])([F:35])[F:36])[CH:28]=2)=[CH:38][CH:39]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 131735710HCID 131735710, compound

Product 1

HCID 90402667HCID 90402667, compoundYield 34.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-(7-(4-chlorobenzyl)-3-methyl-2,6-dioxo-8-(3-(trifluoromethoxy)phenoxy)-2,3,6,7-tetrahydro-1H-purin-1-yl)cyclobutanecarboxylate (59 mg, 0.09 mmol) in THF (3 mL) was added LAH (6.8 mg, 0.18 mmol) in one portion and the mixture was stirred at room temperature for 2 h. The reaction was carefully quenched with ethyl acetate and filtered. The filtrate was concentrated to dryness to give a crude product which was purified via preparative HPLC to give 7-(4-chlorobenzyl)-1-(3-(hydroxymethyl)cyclobutyl)-3-methyl-8-(3-(trifluoromethoxy)phenoxy)-1H-purine-2,6(3H,7H)-dione (17 mg, 34.3% yield) as white solid.

Workup

  1. customThe reaction was carefully quenched with ethyl acetate
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated to dryness
  4. customto give a crude product which
  5. customwas purified via preparative HPLC

Sources & evidence

ORD record
ord-64e2c8b35dd246ce8d3c8264e193b8e8
Source dataset
uspto-grants-2016_06
Patent number
US09359359B2

Reaction notes

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