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

HRID 930799Notes

Reaction equation

HRID 930799 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 232.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of N-(3-bromopropyl)-2,6-dichloropyrimidin-4-amine (2.0 g, 7.02 mmol) in 1,4-dioxane (15 mL) and water (15 mL) was added potassium carbonate (2.0 g, 14.47 mmol), stirred for 2 h at 60° C. and then concentrated. The residue was neutralized to pH˜6 by hydrochloride solution (6M), extracted by ethyl acetate to remove byproduct, and then neutralized by sodium hyroxide (2M) to pH˜7. The water was removed in vacuum to afford the title compound (3.03 g).

Workup

  1. concentrationconcentrated
  2. extractionextracted by ethyl acetate
  3. customto remove byproduct
  4. customThe water was removed in vacuum

Sources & evidence

ORD record
ord-c5de83f88cb348d88166c44d32445a81
Source dataset
uspto-grants-2016_03
Patent number
US09296755B2

Reaction notes

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