Methyl iodide → Ethyl 3-Methyl-7,8-Dimethoxypyrimido[4,5-b]quinolin-4(3H)-One-2-Carboxylate

HRID 1112261Notes

Reaction equation

HRID 1112261 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][C:14]=1[O:15][CH3:16])[N:11]=[C:10]1[N:17]=[C:18]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[NH:19][C:20](=[O:21])[C:9]1=[CH:8]2.I[CH3:28]>CN(C)C=O>[CH3:28][N:19]1[C:20](=[O:21])[C:9]2[C:10](=[N:11][C:12]3[C:7]([CH:8]=2)=[CH:6][C:5]([O:4][CH3:3])=[C:14]([O:15][CH3:16])[CH:13]=3)[N:17]=[C:18]1[C:22]([O:24][CH2:25][CH3:26])=[O:23]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 135445830Pirolate

Product 1

HCID 22752848Ethyl 3-Methyl-7,8-Dimethoxypyrimido[4,5-b]quinolin-4(3H)-One-2-Carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (470 mg. of 50% in oil, 0.011 mole) is added to a slurry of ethyl 7,8-dimethoxypyrimido[4,5-b]quinolin-4(3H)-one-2-carboxylate (3.3 g., 0.01 mole) in N,N-dimethylformamide (75 ml.). The mixture is stirred and heated on a steambath for 10 minutes and then at room temperature for a half hour. It is cooled in an ice-bath and iodomethane (2.19 g., 0.015 mole) added dropwise over a 30 minute period. Following completion of addition, the mixture is stirred for an additional 15 minutes in an ice-bath and then for a half-hour at room temperature. The reaction mixture is poured into ice-water (200 ml.) and the resulting solid filtered off, air-dried, and recrystallized from ethanol to give 2.1 g. of yellow crystals (61.2%); m.p. 211.5° C. (dec.)

Workup

  1. temperatureheated on a steambath for 10 minutes
  2. waitat room temperature for a half hour
  3. temperatureIt is cooled in an ice-bath
  4. additioncompletion of addition
  5. stirringthe mixture is stirred for an additional 15 minutes in an ice-bath
  6. waitfor a half-hour at room temperature
  7. filtrationthe resulting solid filtered off
  8. customair-dried
  9. customrecrystallized from ethanol
  10. customto give 2.1 g

Sources & evidence

ORD record
ord-cd6be5d58a1a4045b36a789230e229e9
Source dataset
uspto-grants-1978_10
Patent number
US04120962

Reaction notes

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