Trimethylsilyldiazomethane → 6-Chloro-2-(3-methyl-3,4-dihydro-2H-pyrazol-3-vi)-3H-quinazolin-4-one

HRID 555259Notes

Reaction equation

HRID 555259 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([C:12]([CH3:14])=[CH2:13])[NH:6][C:5]2=[O:15].[Si]([CH:20]=[N+:21]=[N-:22])(C)(C)C>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([C:12]1([CH3:14])[CH2:13][CH:20]=[N:21][NH:22]1)[NH:6][C:5]2=[O:15]

Participants

4

Reactant 2

HCID 167693TrimethylsilyldiazomethaneHCID 1358145016-Chloro-2-isopropenyl-3H-quinazolin-4-one

Product 1

HCID 1358145086-Chloro-2-(3-methyl-3,4-dihydro-2H-pyrazol-3-vi)-3H-quinazolin-4-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

6-Chloro-2-isopropenyl-3H-quinazolin-4-one (1 mmoL) in THF (5 mL) was treated with TMSCHN2 (1.0 N, 3.0 mmoL) at 50° C. for 4 h. The solvent was removed and the residue was purified by silica gel column chromatography to yield the title compound as a white solid.

Workup

  1. customThe solvent was removed
  2. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-67f79bc1ed954cf3a6db1f118fdec4d6
Source dataset
uspto-grants-2011_11
Patent number
US08053441B2

Reaction notes

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