HCID 76759879, compound → HCID 66913060, compound

HRID 1044660Notes

Reaction equation

HRID 1044660 reaction equation
[NH2:1][C:2]1[C:3]([N:29]2[CH2:34][CH2:33][O:32][CH2:31][CH2:30]2)=[N:4][C:5]([CH:14]=[CH:15][CH:16]=[CH:17][C:18]2[CH:23]=[CH:22][C:21]([N:24]([CH2:27][CH3:28])[CH2:25][CH3:26])=[CH:20][CH:19]=2)=[N:6][C:7]=1[N:8]1[CH2:13][CH2:12][O:11][CH2:10][CH2:9]1>C(O)C.[Pd]>[NH2:1][C:2]1[C:3]([N:29]2[CH2:30][CH2:31][O:32][CH2:33][CH2:34]2)=[N:4][C:5]([CH2:14][CH2:15][CH2:16][CH2:17][C:18]2[CH:19]=[CH:20][C:21]([N:24]([CH2:25][CH3:26])[CH2:27][CH3:28])=[CH:22][CH:23]=2)=[N:6][C:7]=1[N:8]1[CH2:13][CH2:12][O:11][CH2:10][CH2:9]1

Participants

4

Reactant 1

HCID 76759879HCID 76759879, compound2×

Product 1

HCID 66913060HCID 66913060, compoundYield 26%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

The synthesis method shall be explained concretely, and in order, below. 5-amino-2-[4-(4-diethylaminophenyl)butan-1,3-dienyl]-4,6-dimorpholinopyrimidine (500 mg, 1.08 mmol) (Compound 144) was dissolved in ethanol (30 ml), 300 mg of Pd/C was added, and catalytic reduction was carried out for 18 hours at room temperature. The Pd/C was filtered out of the reaction liquid using celite, the filtrate was taken and the solvent was distilled away under reduced pressure. The residue was separated and purified by silica gel chromatography (hexane:ethyl acetate=1:1), and 131.4 mg of 5-amino-2-[4-(4-diethylaminophenyl)butyl]-4,6-dimorpholino pyrimidine (Compound 145) was obtained (yield 26%). The MS measurement result, and the NMR data for the obtained Compound 145 are shown below.

Workup

  1. customThe synthesis method
  2. filtrationThe Pd/C was filtered out of the reaction liquid
  3. distillationthe solvent was distilled away under reduced pressure
  4. customThe residue was separated
  5. custompurified by silica gel chromatography (hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-ebbf4a33b4b64ba784923c19efb4d67b
Source dataset
uspto-grants-2013_10
Patent number
US08563715B2

Reaction notes

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