Benzaldehyde → 2-{1-[2-(1-benzyl-piperidin-4-yl)ethyl]piperidin-4-yloxy}-1-methyl-1H-[4,4']bipyrimidinyl-6-one

HRID 1468785Notes

Reaction equation

HRID 1468785 reaction equation
[CH3:1][N:2]1[C:7](=[O:8])[CH:6]=[C:5]([C:9]2[CH:14]=[CH:13][N:12]=[CH:11][N:10]=2)[N:4]=[C:3]1[O:15][CH:16]1[CH2:21][CH2:20][N:19]([CH2:22][CH2:23][CH:24]2[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]2)[CH2:18][CH2:17]1.[CH:30](=O)[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(O)(=O)C.ClCCCl>[CH2:30]([N:27]1[CH2:26][CH2:25][CH:24]([CH2:23][CH2:22][N:19]2[CH2:18][CH2:17][CH:16]([O:15][C:3]3[N:2]([CH3:1])[C:7](=[O:8])[CH:6]=[C:5]([C:9]4[CH:14]=[CH:13][N:12]=[CH:11][N:10]=4)[N:4]=3)[CH2:21][CH2:20]2)[CH2:29][CH2:28]1)[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Participants

6

Reactant 3

HCID 240BenzaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 679776901-methyl-2-[1-(2-piperidin-4-yl-ethyl)piperidin-4-yloxy]-1H-[4,4']bipyrimidinyl-6-one

Product 1

HCID 679776922-{1-[2-(1-benzyl-piperidin-4-yl)ethyl]piperidin-4-yloxy}-1-methyl-1H-[4,4']bipyrimidinyl-6-oneYield 710%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 111,2-DichloroethaneSolvent

Procedure

To a mixture of 1-methyl-2-[1-(2-piperidin-4-yl-ethyl)piperidin-4-yloxy]-1H-[4,4′]bipyrimidinyl-6-one (40 mg, 0.10 mmol), benzaldehyde (16 mg, 0.15 mmol) and acetic acid (one drop) in 1,2-dichloroethane (0.5 ml) was added sodium triacetoxyborohydride (53 mg, 0.25 mmol). The mixture was stirred at room temperature overnight. The mixture was partitioned between water and dichloromethane. The organic layer was washed with brine, dried over sodium sulfate, and concentrated in vacuo. The residue was purified by NH-silica gel column chromatography (eluent; hexane/ethyl acetate=20/80) to afford 2-{1-[2-(1-benzyl-piperidin-4-yl)ethyl]piperidin-4-yloxy}-1-methyl-1H-[4,4′]bipyrimidinyl-6-one as a colorless solid (35 mg, 0.71 mmol, 71%).

Workup

  1. customThe mixture was partitioned between water and dichloromethane
  2. washThe organic layer was washed with brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by NH-silica gel column chromatography (eluent; hexane/ethyl acetate=20/80)

Sources & evidence

ORD record
ord-02b9b0bfe8284aeabd4d6282df17c867
Source dataset
uspto-grants-2015_04
Patent number
US09006232B2

Reaction notes

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