Dimethylformamide → HCID 59184688, compound

HRID 426147Notes

Reaction equation

[CH:1]([C:4]1[C:9](=[O:10])[NH:8][C:7](=[O:11])[NH:6][C:5]=1OC1C=C(C=C(C)C=1)C#N)([CH3:3])[CH3:2].[C:22](=[O:25])([O-])[O-].[K+].[K+].[I-].[Li+].Cl[CH2:31][C:32]1[CH:37]=[CH:36][N:35]=[C:34]([N:38]2[C:46](=[O:47])[C:45]3[C:40](=[CH:41][CH:42]=[CH:43][CH:44]=3)[C:39]2=[O:48])[CH:33]=1.C[N:50]([CH:52]=O)C>>[O:48]=[C:39]1[C:40]2[C:45](=[CH:44][CH:43]=[CH:42][CH:41]=2)[C:46](=[O:47])[N:38]1[C:34]1[CH:33]=[C:32]([CH2:31][N:6]2[C:5]([C:22]([C:44]3[CH:43]=[C:42]([CH:41]=[C:40]([CH3:39])[CH:45]=3)[C:52]#[N:50])=[O:25])=[C:4]([CH:1]([CH3:2])[CH3:3])[C:9](=[O:10])[NH:8][C:7]2=[O:11])[CH:37]=[CH:36][N:35]=1

Participants

Reactant 5

HCID 6228Dimethylformamide

HCID 11430Potassium Carbonate

HCID 66321Lithium iodide

HCID 591846992-[4-(Chloromethyl)-2-pyridinyl]-1H-isoindole-1,3(2H)-dione

HCID 596868373-(5-Isopropyl-2,6-dioxo-1,2,3,6-tetrahydro-pyrimidin-4-yloxy)-5-methyl-benzonitrile

Product 1

HCID 59184688HCID 59184688, compoundYield 41%

Procedure

To a stirred solution of (73) (297 mg, 1 mmol), anhydrous powdered potassium carbonate (134 mg, 1 mmol), and lithium iodide (134 mg, 1 mmol) in DMF (5 ml) at room temperature, was added 2-(4-Chloromethyl-pyridin-2-yl)-isoindole-1,3-dione (272 mg, 1 mmol). After stirring for overnight, the mixture was evaporated in vacuo and the residue was purified by silica gel column chromatography (eluent, EA:hexanes (1:1); Rf˜0.2 fraction was collected.) to afford 205 mg (41%) of a white solid.

Workup

customthe mixture was evaporated in vacuo
customthe residue was purified by silica gel column chromatography (eluent, EA:hexanes (1:1); Rf˜0.2 fraction was collected.)

Sources & evidence

ORD record: ord-9e795b1b0d964b97b2763652e81dec6d
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08106064B2

Reaction notes

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