HCID 21851516, compound → HCID 9932517, compound

HRID 617190Notes

Reaction equation

HRID 617190 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([O:15]CC3C=CC=CC=3)=[CH:11][CH:10]=2)[CH:5]=[C:4]([CH:23]2[CH2:28][CH2:27][N:26]([C:29](=[O:39])[C:30]3[CH:35]=[CH:34][C:33]4[O:36][CH2:37][O:38][C:32]=4[CH:31]=3)[CH2:25][CH2:24]2)[N:3]=1>C(O)(=O)C.[Pd]>[NH2:1][C:2]1[N:7]=[C:6]([CH2:8][C:9]2[CH:10]=[CH:11][C:12]([OH:15])=[CH:13][CH:14]=2)[CH:5]=[C:4]([CH:23]2[CH2:28][CH2:27][N:26]([C:29](=[O:39])[C:30]3[CH:35]=[CH:34][C:33]4[O:36][CH2:37][O:38][C:32]=4[CH:31]=3)[CH2:25][CH2:24]2)[N:3]=1

Participants

4

Reactant 1

HCID 21851516HCID 21851516, compound

Product 1

HCID 9932517HCID 9932517, compoundYield 54.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

2-Amino-4-(4-benzyloxyphenylmethyl)-6-[1-(3,4-methylenedioxybenzoyl)-4-piperidinyl]pyrimidine (570 mg, 1.09 mmol) was dissolved in acetic acid (5 ml) and hydrogenated under 1 atm in the presence of 10% palladium on carbon (360 mg) for about 3.5 hours. The catalyst was filtered off. The filtrate was poured into aqueous sodium hydrogen carbonate and extracted with chloroform. The organic layer was concentrated in vacuo and the residue was purified by column chromatography (chloroform:methanol=97:3) to give the titled compound (256 mg) as a foam.

Workup

  1. filtrationThe catalyst was filtered off
  2. additionThe filtrate was poured into aqueous sodium hydrogen carbonate
  3. extractionextracted with chloroform
  4. concentrationThe organic layer was concentrated in vacuo
  5. customthe residue was purified by column chromatography (chloroform:methanol=97:3)

Sources & evidence

ORD record
ord-fc84e7be9587420482c41d6282f9a1ef
Source dataset
uspto-grants-1999_09
Patent number
US05948786

Reaction notes

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