Sodium Cyanate → 3-(N-Carbamoyl-4-aminobutyl)-9,10-dimethoxy-2-(2,4,6-trimethylphenylimino)-3,4,6,7-tetrahydro-2H-pyrimido[6,1-a]isoquinolin-4-one

HRID 1007169Notes

Reaction equation

HRID 1007169 reaction equation
[O-:1][C:2]#[N:3].[Na+].NCCCC[C:10]1[C:11](=[N:29][C:30]2[C:35]([CH3:36])=[CH:34][C:33]([CH3:37])=[CH:32][C:31]=2[CH3:38])[NH:12][C:13](=[O:28])[N:14]2[CH2:23][CH2:22][C:21]3[C:16](=[CH:17][C:18]([O:26][CH3:27])=[C:19]([O:24][CH3:25])[CH:20]=3)[C:15]=12>O.Cl>[C:2]([NH:12][CH2:11][CH2:10][CH2:15][CH2:16][N:12]1[C:11](=[N:29][C:30]2[C:31]([CH3:38])=[CH:32][C:33]([CH3:37])=[CH:34][C:35]=2[CH3:36])[CH:10]=[C:15]2[C:16]3[C:21]([CH2:22][CH2:23][N:14]2[C:13]1=[O:28])=[CH:20][C:19]([O:24][CH3:25])=[C:18]([O:26][CH3:27])[CH:17]=3)(=[O:1])[NH2:3]

Participants

5

Reactant 2

HCID 517096Sodium CyanateHCID 178486492HCID 178486492, compound

Product 1

HCID 99359563-(N-Carbamoyl-4-aminobutyl)-9,10-dimethoxy-2-(2,4,6-trimethylphenylimino)-3,4,6,7-tetrahydro-2H-pyrimido[6,1-a]isoquinolin-4-oneYield 128.2%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent2×

Conditions

Temperature
80 °C

Procedure

Sodium cyanate (0.28 g, 4.32 mmol) in water (6 ml) was added dropwise to a stirred solution of 2 (1.0 g, 2.16 mmol) in water (30 ml) and 1N HCl (4.3 ml) at 80° C. After 2 h at 80° C. the mixture was cooled and extracted with dichloromethane (3×20 ml) and the extract dried (MgSO4) and evaporated in vacuo. The residue was purified by column chromatography on silica gel [dichloromethane/methanol (97:3)] to obtain the title compound (0.70 g, 64%) as a yellow solid.

Workup

  1. extractionextracted with dichloromethane (3×20 ml)
  2. dry with materialthe extract dried (MgSO4)
  3. customevaporated in vacuo
  4. customThe residue was purified by column chromatography on silica gel [dichloromethane/methanol (97:3)]

Sources & evidence

ORD record
ord-c63b673b71dd41a28697736df751e6b2
Source dataset
uspto-grants-2004_09
Patent number
US06794391B2

Reaction notes

Loading…