Hydrochloric Acid → Urea, N-[2-[6,7-dihydro-9,10-dimethoxy-4-oxo-2-[(2,4,6-trimethylphenyl)imino]-2H-pyrimido[6,1-a]isoquinolin-3(4H)-yl]ethyl]-

HRID 2224192Notes

Reaction equation

HRID 2224192 reaction equation
[O-:1][C:2]#[N:3].[Na+].[CH3:5][O:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][C:16]=1[O:17][CH3:18])[C:13]1=[CH:19][C:20](=[N:27][C:28]3[C:33]([CH3:34])=[CH:32][C:31]([CH3:35])=[CH:30][C:29]=3[CH3:36])[N:21]([CH2:24][CH2:25][NH2:26])[C:22](=[O:23])[N:12]1[CH2:11][CH2:10]2.Cl.[OH-].[Na+]>O>[CH3:5][O:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][C:16]=1[O:17][CH3:18])[C:13]1=[CH:19][C:20](=[N:27][C:28]3[C:29]([CH3:36])=[CH:30][C:31]([CH3:35])=[CH:32][C:33]=3[CH3:34])[N:21]([CH2:24][CH2:25][NH:26][C:2](=[O:1])[NH2:3])[C:22](=[O:23])[N:12]1[CH2:11][CH2:10]2

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 517096Sodium CyanateHCID 219584924H-?Pyrimido[6,?1-?a]?isoquinolin-?4-?one, 3-?(2-?aminoethyl)?-?2,?3,?6,?7-?tetrahydro-?9,?10-?dimethoxy-?2-?[(2,?4,?6-?trimethylphenyl)?imino]?-

Product 1

HCID 9934746Urea, N-[2-[6,7-dihydro-9,10-dimethoxy-4-oxo-2-[(2,4,6-trimethylphenyl)imino]-2H-pyrimido[6,1-a]isoquinolin-3(4H)-yl]ethyl]-

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
80 °C

Procedure

Sodium cyanate (6.0 g, 0.092 mol) in water (100 ml) was added dropwise to a stirred solution of 9,10-Dimethoxy-2-(2,4,6-trimethylphenylimino)-3-(2-aminoethyl)-3,4,6,7-tetrahydro-2H-pyrimido[6,1-a]isoquinolin-4-one, prepared according to Preparation 4 above (20.0 g, 0.046 mol) in water (600 ml) and 1N HCl (92 ml) at 80° C. After stirring for 2 h at 80° C. the mixture was cooled in an ice-bath and basified with 2N NaOH. The mixture was extracted with dichloromethane (3×200 ml) and the combined extract was dried (MgSO4) and evaporated in vacuo. The resulting yellow foam was purified by column chromatography on silica gel eluting with CH2Cl2/MeOH (97:3) and triturated with ether to obtain the title compound as a yellow solid, 11.9 g, 54%.

Workup

  1. customprepared
  2. customat 80° C
  3. temperaturewas cooled in an ice-bath
  4. extractionThe mixture was extracted with dichloromethane (3×200 ml)
  5. extractionthe combined extract
  6. dry with materialwas dried (MgSO4)
  7. customevaporated in vacuo
  8. customThe resulting yellow foam was purified by column chromatography on silica gel eluting with CH2Cl2/MeOH (97:3)
  9. customtriturated with ether

Sources & evidence

ORD record
ord-a6ab621c3ece4075b39fac8c93b605d4
Source dataset
uspto-grants-2008_05
Patent number
US07378424B2

Reaction notes

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