Potassium Carbonate → 4-[(3R)-3-Methyl-4-(1-methyl-6-oxo-1,6-dihydro-[4,4']bipyrimidinyl-2-yl)-piperazin-1-yl]-benzonitrile

HRID 1045695Notes

Reaction equation

HRID 1045695 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].F[C:23]1[CH:30]=[CH:29][C:26]([C:27]#[N:28])=[CH:25][CH:24]=1.C(=O)([O-])[O-].[K+].[K+]>>[CH3:21][C@H:16]1[N:15]([C:3]2[N:2]([CH3:1])[C:7](=[O:8])[CH:6]=[C:5]([C:9]3[CH:14]=[CH:13][N:12]=[CH:11][N:10]=3)[N:4]=2)[CH2:20][CH2:19][N:18]([C:23]2[CH:30]=[CH:29][C:26]([C:27]#[N:28])=[CH:25][CH:24]=2)[CH2:17]1

Participants

4

Reactant 3

HCID 11430Potassium CarbonateHCID 145174-FluorobenzonitrileHCID 250045961-methyl-2-((2R)-2-methyl-piperazin-1-yl)-1H-[4,4']bipyrimidinyl-6-one

Product 1

HCID 578700144-[(3R)-3-Methyl-4-(1-methyl-6-oxo-1,6-dihydro-[4,4']bipyrimidinyl-2-yl)-piperazin-1-yl]-benzonitrileYield 84%

Conditions

Temperature
120 °C

Procedure

To a stirred solution of 1-Methyl-2-((2R)-2-methyl-piperazin-1-yl)-1H-[4,4′]bipyrimidinyl-6-one (1.50 g, 5.24 mmol) in dimethyl sulufoxide (10.0 ml) was added 4-fluorobenzonitrile (1.27 g, 10.5 mmol), potassium carbonate (2.90 g, 21.0 mmol), and the reaction mixture was stirred for 12 hours at 120° C. The reaction was quenched with water, the aqueous layer was extracted with ethyl acetate. The extract was washed with water and brine, dried over magnesium sulfate, and concentrated in vacuo. After removal of the solvent, the precipitate was filtered, washed with ether, and dried to give 4-[(3R)-3-Methyl-4-(1-methyl-6-oxo-1,6-dihydro-[4,4′]bipyrimidinyl-2-yl)-piperazin-1-yl]-benzonitrile (1.70 g, 4.39 mmol, 84%) as pale yellow crystals.

Workup

  1. customThe reaction was quenched with water
  2. extractionthe aqueous layer was extracted with ethyl acetate
  3. washThe extract was washed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customAfter removal of the solvent
  7. filtrationthe precipitate was filtered
  8. washwashed with ether
  9. customdried

Sources & evidence

ORD record
ord-3ce368620c184cd08e33686fe95d4a7a
Source dataset
uspto-grants-2013_10
Patent number
US08569294B2

Reaction notes

Loading…