HCID 21473602, compound → HCID 21473635, compound

HRID 2294028Notes

Reaction equation

HRID 2294028 reaction equation
[CH2:1]([O:8][CH2:9][C:10]1[CH2:11][CH2:12][N:13]([CH2:16][C:17]2[C:18]([NH2:24])=[N:19][C:20]([CH3:23])=[N:21][CH:22]=2)[CH2:14][CH:15]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>O1CCCC1.[Pt](=O)=O>[CH2:1]([O:8][CH2:9][CH:10]1[CH2:15][CH2:14][N:13]([CH2:16][C:17]2[C:18]([NH2:24])=[N:19][C:20]([CH3:23])=[N:21][CH:22]=2)[CH2:12][CH2:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 21473602HCID 21473602, compound

Product 1

HCID 21473635HCID 21473635, compoundYield 70.3%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

A suspension of 0.040 g of platinum dioxide in 2 ml of tetrahydrofuran was treated with a solution of 0.11 g (0.00034 mol) of [5-(4-benzyloxymethyl-3,6-dihydro-2H-pyridin-1-ylmethyl)-2-methyl-pyrimidin-4-yl]-amine in 3.5 ml of tetrahydrofuran and the mixture was hydrogenated under normal pressure for 5 hours. The catalyst was filtered off, the filtrate was concentrated and the residue was chromatographed on silica gel with ethyl acetate as the eluent. 0.078 g (70%) of [5-(4-benzyloxymethyl-piperidin-1-ylmethyl)-2-methyl-pyrimidin-4-yl]-amine was obtained as colourless crystals; m.p. 106°-108°.

Workup

  1. filtrationThe catalyst was filtered off
  2. concentrationthe filtrate was concentrated
  3. customthe residue was chromatographed on silica gel with ethyl acetate as the eluent

Sources & evidence

ORD record
ord-81b6e28b55384f87bcba271d16bb6d97
Source dataset
uspto-grants-1997_11
Patent number
US05688798

Reaction notes

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