Ethyl acetate hexane → HCID 23152957, compound

HRID 492717Notes

Reaction equation

HRID 492717 reaction equation
[N:1]1([C:6]([NH:8][C:9]2[N:14]=[CH:13][N:12]=[C:11]([NH:15][C:16]3[CH:21]=[CH:20][C:19]([NH:22]C(=O)OCC4C=CC=CC=4)=[CH:18][CH:17]=3)[CH:10]=2)=[O:7])[CH2:5][CH2:4][CH2:3][CH2:2]1.[H][H].CCCCCC.C(OCC)(=O)C>O1CCCC1.CO.[C].[Pd]>[NH2:22][C:19]1[CH:18]=[CH:17][C:16]([NH:15][C:11]2[CH:10]=[C:9]([NH:8][C:6]([N:1]3[CH2:5][CH2:4][CH2:3][CH2:2]3)=[O:7])[N:14]=[CH:13][N:12]=2)=[CH:21][CH:20]=1

Participants

7

Reactant 3

HCID 21226206Ethyl acetate hexaneHCID 23153357HCID 23153357, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 23152957HCID 23152957, compoundYield 71.1%

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Benzyl N-{4-[6-(pyrrolidin-1-ylcarbonyl)aminopyrimidin-4-ylamino]phenyl]carbamate (210 mg) was dissolved in tetrahydrofuran (5 ml)-methanol (5 ml), and then 10% palladium carbon (200 mg) was added thereto under a nitrogen atmosphere, followed by replacing with hydrogen inside the system and stirring for 5 hrs. After replacing with nitrogen inside the system, the reaction mixture was filtered to remove the catalyst, which was washed with tetrahydrofuran and ethanol in this order. The filtrate was concentrated under a reduced pressure to give a residue, to which hexane-ethyl acetate was added to precipitate crystals. The crystals were filtered, and dried under aeration to provide the titled compound (103 mg, 71%) as white crystals.

Workup

  1. filtrationthe reaction mixture was filtered
  2. customto remove the catalyst, which
  3. washwas washed with tetrahydrofuran and ethanol in this order
  4. concentrationThe filtrate was concentrated under a reduced pressure
  5. customto give a residue
  6. customto precipitate crystals
  7. filtrationThe crystals were filtered
  8. customdried under aeration

Sources & evidence

ORD record
ord-8da402d8b0ad45f084ea9f9f0afb38a5
Source dataset
uspto-grants-2009_05
Patent number
US07531532B2

Reaction notes

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