Potassium Iodide → HCID 59131972, compound

HRID 1993092Notes

Reaction equation

HRID 1993092 reaction equation
Cl[CH2:2][CH2:3][CH2:4][N:5]1[CH2:10][CH2:9][CH2:8][N:7]([CH:11]([CH:15]([CH3:17])[CH3:16])[C:12]([OH:14])=[O:13])[C:6]1=[O:18].[C:19]1(=[O:29])[NH:23][C:22](=[O:24])[C:21]2=[CH:25][CH:26]=[CH:27][CH:28]=[C:20]12.[K].[I-].[K+]>CN(C)C=O>[O:24]=[C:22]1[C:21]2[C:20](=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:19](=[O:29])[N:23]1[CH2:2][CH2:3][CH2:4][N:5]1[CH2:10][CH2:9][CH2:8][N:7]([CH:11]([CH:15]([CH3:17])[CH3:16])[C:12]([OH:14])=[O:13])[C:6]1=[O:18]

Participants

5

Reactant 3

HCID 4875Potassium IodideHCID 24194345Phthalimide potassium saltHCID 59131441HCID 59131441, compound

Product 1

HCID 59131972HCID 59131972, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

As a further illustration, Scheme 28, Example 2 depicts the reaction of the chloro-propyl tetrahydropyrimidine derivative 28.13 with potassium phthalimide 28.16. Equimolar amounts of the reactants are combined in dimethylformamide at ca 80°, in the presence of a catalytic amount of potassium iodide, to afford 2-{3-[3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-propyl]-2-oxo-tetrahydro-pyrimidin-1-yl}-3-methyl-butyric acid 28.17. The product is then reacted under reductive amination conditions, as described above (Scheme 10) with a dialkyl formylphenyl phosphonate 28.19 (Epsilon) to yield the phosphonate ester product 28.20.

Sources & evidence

ORD record
ord-b09d0a5461cf439dac5e2df09b76caee
Source dataset
uspto-grants-2010_01
Patent number
US07649015B2

Reaction notes

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