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 2213713Notes

Reaction equation

[O-:1][C:2]#[N:3].[Na+].[NH2:5][CH2:6][CH2:7][CH2:8][CH2:9][N:10]1[C:27](=[N:28][C:29]2[C:34]([CH3:35])=[CH:33][C:32]([CH3:36])=[CH:31][C:30]=2[CH3:37])[CH:26]=[C:13]2[C:14]3[C:19]([CH2:20][CH2:21][N:12]2[C:11]1=[O:38])=[CH:18][C:17]([O:22][CH3:23])=[C:16]([O:24][CH3:25])[CH:15]=3>O.Cl>[C:2]([NH:5][CH2:6][CH2:7][CH2:8][CH2:9][N:10]1[C:27](=[N:28][C:29]2[C:34]([CH3:35])=[CH:33][C:32]([CH3:36])=[CH:31][C:30]=2[CH3:37])[CH:26]=[C:13]2[C:14]3[C:19]([CH2:20][CH2:21][N:12]2[C:11]1=[O:38])=[CH:18][C:17]([O:22][CH3:23])=[C:16]([O:24][CH3:25])[CH:15]=3)(=[O:1])[NH2:3]

Participants

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

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

Sources & evidence

ORD record: ord-1a3cef5bde104658b2cc46f36e7a84b7
Source dataset: uspto-grants-2006_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07105663B2

Reaction notes

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