Sodium Iodide → HCID 49764660, compound

HRID 1022493Notes

Reaction equation

HRID 1022493 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH:12]1[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1)[C:7](=[O:18])[N:6]([CH2:19][C:20]1[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[C:22]([O:28][CH3:29])[CH:21]=1)[C:5]2=[O:30].[CH2:31](Br)[C:32]#[CH:33].C([O-])([O-])=O.[K+].[K+].[I-].[Na+]>CN(C=O)C>[CH3:29][O:28][C:22]1[CH:21]=[C:20]([CH:25]=[CH:24][C:23]=1[O:26][CH3:27])[CH2:19][N:6]1[C:5](=[O:30])[C:4]2[C:9](=[CH:10][CH:11]=[C:2]([NH:1][CH2:33][C:32]#[CH:31])[CH:3]=2)[N:8]([CH:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)[C:7]1=[O:18]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 7842Propargyl bromideHCID 11430Potassium CarbonateHCID 497630596-amino-3-(3,4-dimethoxybenzyl)-1-(tetrahydro-2H-pyran-4-yl)quinazoline-2,4(1H,3H)-dione

Product 1

HCID 49764660HCID 49764660, compoundYield 56.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 0.25 g of the compound obtained in Step 6.4, 0.094 g of propargyl bromide, 0.12 g of K2CO3 and 0.009 g of sodium iodide in 8.25 ml of DMF is irradiated in a microwave field for 3 hours at 100° C. The resulting mixture is evaporated under reduced pressure. The residue is chromatographed on silica gel, eluting with an MeOH/DCM mixture from (0/100) to (2/98, v/v) to give 0.155 g of the expected product.

Workup

  1. customis irradiated in a microwave field for 3 hours at 100° C
  2. customThe resulting mixture is evaporated under reduced pressure
  3. customThe residue is chromatographed on silica gel
  4. washeluting with an MeOH/DCM mixture from (0/100) to (2/98, v/v)

Sources & evidence

ORD record
ord-056cc959bd8443abb869a10c618462cb
Source dataset
uspto-grants-2014_05
Patent number
US08722659B2

Reaction notes

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