Lithium → HCID 59362878, compound

HRID 1668825Notes

Reaction equation

HRID 1668825 reaction equation
[Li].[N:2]1([C:8]2[N:13]=[C:12]([NH:14][C:15]3[CH:20]=[CH:19][C:18]([C:21]4([C:26](O)=[O:27])[CH2:25][CH2:24][CH2:23][CH2:22]4)=[CH:17][CH:16]=3)[C:11]3[CH2:29][CH2:30][CH2:31][C:10]=3[N:9]=2)[CH2:7][CH2:6][O:5][CH2:4][CH2:3]1>O1CCCC1>[N:2]1([C:8]2[N:13]=[C:12]([NH:14][C:15]3[CH:16]=[CH:17][C:18]([C:21]4([CH2:26][OH:27])[CH2:22][CH2:23][CH2:24][CH2:25]4)=[CH:19][CH:20]=3)[C:11]3[CH2:29][CH2:30][CH2:31][C:10]=3[N:9]=2)[CH2:7][CH2:6][O:5][CH2:4][CH2:3]1

Participants

4

Reactant 2

HCID 3028194LithiumHCID 59362939HCID 59362939, compound

Product 1

HCID 59362878HCID 59362878, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Lithium aluminumhydride (2M solution in tetrahydrofuran, 1.0 mL) was added drop-wise to a solution of 1-[4-(2-morpholin-4-yl-6,7-dihydro-5H-cyclopentapyrimidin-4-ylamino)-phenyl]-cyclopentanecarboxylic acid (0.3 g, 0.73 mmol) prepared using a procedure as described in example 22; in anhydrous tetrahydrofuran (10 mL) at 0° C. to 5° C. After addition, the reaction mixture was warmed to a temperature in the range of 15° C. to 40° C. and stirring continued for an additional 10 hours. The reaction was quenched by addition of aqueous sodium hydroxide. The precipitated solid was filtered and washed with ethyl acetate. The combined filtrates were washed with brine, dried over Na2SO4, filtered, and concentrated. The residue was purified by column chromatography (silica gel) to afford the title compound as a white solid (0.11 g, 39% yield).

Workup

  1. customprepared
  2. customat 0° C. to 5° C
  3. additionAfter addition
  4. temperaturethe reaction mixture was warmed to a temperature in the range of 15° C. to 40° C.
  5. customThe reaction was quenched by addition of aqueous sodium hydroxide
  6. filtrationThe precipitated solid was filtered
  7. washwashed with ethyl acetate
  8. washThe combined filtrates were washed with brine
  9. dry with materialdried over Na2SO4
  10. filtrationfiltered
  11. concentrationconcentrated
  12. customThe residue was purified by column chromatography (silica gel)

Sources & evidence

ORD record
ord-06dde3688b0d43ada9bd86f95ea57de8
Source dataset
uspto-grants-2011_08
Patent number
US07989463B2

Reaction notes

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