Lithium → HCID 59362904, compound

HRID 1668824Notes

Reaction equation

HRID 1668824 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:25](O)=[O:26])[CH2:24][CH2:23][CH2:22]4)=[CH:17][CH:16]=3)[C:11]3[CH2:28][CH2:29][CH2:30][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([CH2:25][OH:26])[CH2:24][CH2:23][CH2:22]4)=[CH:19][CH:20]=3)[C:11]3[CH2:28][CH2:29][CH2:30][C:10]=3[N:9]=2)[CH2:7][CH2:6][O:5][CH2:4][CH2:3]1

Participants

4

Reactant 2

HCID 3028194LithiumHCID 59362928HCID 59362928, compound

Product 1

HCID 59362904HCID 59362904, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Lithium aluminumhydride (2M solution in tetrahydrofuran, 1.5 mL) was added drop-wise to a solution of 1-[4-(2-morpholin-4-yl-6,7-dihydro-5H-cyclopentapyrimidin-4-ylamino)-phenyl]-cyclobutanecarboxylic acid (0.61 g, 1.52 mmol) 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 to yield a white solid. The title compound was afforded following purification by column chromatography (silica gel) as a white solid (0.56 g, 80% yield).

Workup

  1. additionAfter addition
  2. temperaturethe reaction mixture was warmed to a temperature in the range of 15° C. to 40° C.
  3. customThe reaction was quenched by addition of aqueous sodium hydroxide
  4. filtrationThe precipitated solid was filtered
  5. washwashed with ethyl acetate
  6. washThe combined filtrates were washed with brine
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customto yield a white solid

Sources & evidence

ORD record
ord-da7e497459f648159e7ee855fbe300da
Source dataset
uspto-grants-2011_08
Patent number
US07989463B2

Reaction notes

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