HCID 90020504, compound → HCID 90020621, compound

HRID 2200094Notes

Reaction equation

HRID 2200094 reaction equation
[N+:1]([C:4]1[CH:22]=[CH:21][C:7]([O:8][C:9]2[N:14]=[CH:13][N:12]=[C:11]([NH:15][C:16]([CH:18]3[CH2:20][CH2:19]3)=[O:17])[CH:10]=2)=[CH:6][CH:5]=1)([O-])=O>C(Cl)Cl.[Pd]>[NH2:1][C:4]1[CH:22]=[CH:21][C:7]([O:8][C:9]2[N:14]=[CH:13][N:12]=[C:11]([NH:15][C:16]([CH:18]3[CH2:19][CH2:20]3)=[O:17])[CH:10]=2)=[CH:6][CH:5]=1

Participants

4

Reactant 1

HCID 90020504HCID 90020504, compound

Product 1

HCID 90020621HCID 90020621, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6344DichloromethaneSolvent

Procedure

Dissolve N-[6-(4-nitrophenoxyl)pyrimidin-4-yl]cyclopropanecarboxamide (2.2 g, 7.33 mmol) in DCM (50 mL), add Pd/C (10%, 340 mg), flush with H2, and stir at room temperature under H2 for 2 hrs. After the reaction is complete, flush with N2, and then filter, concentrate the filtrate, purify the crude product by chromatography (silica gel, EtOAc:PE=1:1) to provide the title compound (1.8 g, 91%). MS: (M+1): 271.

Workup

  1. customflush with H2
  2. customflush with N2
  3. filtrationfilter
  4. concentrationconcentrate the filtrate
  5. custompurify the crude product by chromatography (silica gel, EtOAc:PE=1:1)

Sources & evidence

ORD record
ord-b1a8311c47a6406490d81e31e1d0f7cd
Source dataset
uspto-grants-2016_06
Patent number
US09359338B2

Reaction notes

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