Potassium Carbonate → 1-methyl-2-{(2R)-2-methyl-4-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)-benzyl]-piperazin-1-yl}-1H-[4,4']bipyrimidinyl-6-one

HRID 1045698Notes

Reaction equation

HRID 1045698 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[N:15]1[CH2:20][CH2:19][NH:18][CH2:17][C@H:16]1[CH3:21].C(=O)([O-])[O-].[K+].[K+].Br[CH2:29][C:30]1[CH:35]=[CH:34][C:33]([C:36]2[N:40]=[C:39]([CH3:41])[O:38][N:37]=2)=[CH:32][CH:31]=1>CN(C)C=O>[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[N:15]1[CH2:20][CH2:19][N:18]([CH2:29][C:30]2[CH:31]=[CH:32][C:33]([C:36]3[N:40]=[C:39]([CH3:41])[O:38][N:37]=3)=[CH:34][CH:35]=2)[CH2:17][C@H:16]1[CH3:21]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 71645903-(4-(Bromomethyl)phenyl)-5-methyl-1,2,4-oxadiazoleHCID 250045961-methyl-2-((2R)-2-methyl-piperazin-1-yl)-1H-[4,4']bipyrimidinyl-6-one

Product 1

HCID 578698601-methyl-2-{(2R)-2-methyl-4-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)-benzyl]-piperazin-1-yl}-1H-[4,4']bipyrimidinyl-6-oneYield 63%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-methyl-2-((2R)-2-methyl-piperazin-1-yl)-1H-[4,4′]bipyrimidinyl-6-one (0.15 g, 0.52 mmol) and potassium carbonate (0.22 g, 1.59 mmol) in N,N-dimethylformamide (1.5 ml) was added 3-[4-(bromomethyl)phenyl]-5-methyl-1,2,4-oxadiazole (0.14 g, 0.55 mmol) at room temperature and the mixture was stirred for 4 hours. The mixture was partitioned between water and dichloromethane, and the organic layer was washed with water, brine, and dried over sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent; ethyl acetate) to afford 1-methyl-2-{(2R)-2-methyl-4-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)-benzyl]-piperazin-1-yl}-1H-[4,4′]bipyrimidinyl-6-one (0.15 g, 63%).

Workup

  1. customThe mixture was partitioned between water and dichloromethane
  2. washthe organic layer was washed with water, brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (eluent; ethyl acetate)

Sources & evidence

ORD record
ord-ad98122cfc56480bb8732737608a1a3c
Source dataset
uspto-grants-2013_10
Patent number
US08569294B2

Reaction notes

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