Potassium Carbonate → 8-Chloro-3,4-dihydro-1H-pyrimido[1,6-A]pyrimidin-6(2H)-one

HRID 920361Notes

Reaction equation

HRID 920361 reaction equation
Br[CH2:2][CH2:3][CH2:4][NH:5][C:6]1[CH:11]=[C:10]([Cl:12])[N:9]=[C:8](Cl)[N:7]=1.C(=O)([O-])[O-:15].[K+].[K+]>O1CCOCC1.O>[Cl:12][C:10]1[CH:11]=[C:6]2[NH:5][CH2:4][CH2:3][CH2:2][N:7]2[C:8](=[O:15])[N:9]=1

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 86676391N-(3-bromopropyl)-2,6-dichloropyrimidin-4-amine

Product 1

HCID 1357418828-Chloro-3,4-dihydro-1H-pyrimido[1,6-A]pyrimidin-6(2H)-oneYield 55.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
60 °C

Procedure

A suspension of N-(3-bromopropyl)-2,6-dichloropyrimidin-4-amine (47 g, 165 mmol) and potassium carbonate (68.4 g, 495 mmol) in 1,4-dioxane (100 mL) and water (100 mL), was heated to 60° C. overnight. The mixture was evaporated to remove the dioxane solvent and the mixture was adjusted to pH ˜6 with HCl (6M). The mixture was extracted with ethyl acetate to remove by product and aqueous phase was adjusted to pH ˜7 with NaOH (2M), evaporated to afford the title compound (17 g, 55% yield).

Workup

  1. customThe mixture was evaporated
  2. customto remove the dioxane solvent
  3. extractionThe mixture was extracted with ethyl acetate
  4. customto remove by product and aqueous phase
  5. customevaporated

Sources & evidence

ORD record
ord-363685049e044985bc56aceed9d34aa9
Source dataset
uspto-grants-2016_03
Patent number
US09273054B2

Reaction notes

Loading…