Methyl iodide → HCID 19006278, compound

HRID 1742932Notes

Reaction equation

HRID 1742932 reaction equation
[H-].[Na+].[C:3]([NH:11][C:12]1[CH:21]=[CH:20][C:19]2[N:18]([CH3:22])[C:17]3=[CH:23][C:24]([C:26]([O:28]CC)=[O:27])=[N:25][N:16]3[C:15](=[O:31])[C:14]=2[CH:13]=1)(=[O:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.I[CH3:33]>CN(C=O)C>[C:3]([N:11]([CH3:33])[C:12]1[CH:21]=[CH:20][C:19]2[N:18]([CH3:22])[C:17]3=[CH:23][C:24]([C:26]([OH:28])=[O:27])=[N:25][N:16]3[C:15](=[O:31])[C:14]=2[CH:13]=1)(=[O:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 86748094HCID 86748094, compound

Product 1

HCID 19006278HCID 19006278, compoundYield 57.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
0 °C

Procedure

To a stirring suspension of sodium hydride (0.05 9, 1.25 mmol, 60% dispersion in mineral oil) in 20 mL of DMF was added dropwise a solution of 7-(benzoylamino)-4,9-dihydro-4-methyl-9-oxopyrazolo-[5,1-b]quinazoline-2-carboxylic acid, ethyl ester (0.40 g, 1.02 mmol, Example 2) in 30 mL of DMF. The mixture was stirred for 30 minutes at 0° C. followed by dropwise addition of iodomethane (0.07 mL, 1.12 mmol). The ice-bath was removed, the mixture was stirred at room temperature for 2 hours, then concentrated to a yellow solid. The solid was dissolved into water, acidified to a pH of about 7 with a saturated solution of potassium phosphate, monobasic, and extracted into chloroform (2×50 mL). The combined chloroform extract was dried (MgSO4), filtered, and concentrated. Medium pressure chromatography (silica gel, 2.5% methanol in chloroform) of the crude afforded 0.22 g (52%) of the title compound as its ethyl ester; yellow solid, mp 214°-217° C.

Workup

  1. customThe ice-bath was removed
  2. stirringthe mixture was stirred at room temperature for 2 hours
  3. concentrationconcentrated to a yellow solid
  4. dissolutionThe solid was dissolved into water
  5. extractionmonobasic, and extracted into chloroform (2×50 mL)
  6. extractionThe combined chloroform extract
  7. dry with materialwas dried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-d5ba13a441824706a449dd827244090e
Source dataset
uspto-grants-1994_08
Patent number
US05342942

Reaction notes

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