HCID 178439403, compound → 7-methoxy-8-methyl-2-(3-propan-2-ylpyrazol-1-yl)-1H-quinazolin-4-one

HRID 1443491Notes

Reaction equation

HRID 1443491 reaction equation
Cl[C:2]1[N:11]=[C:10]([OH:12])[C:9]2[C:4](=[C:5]([CH3:15])[C:6]([O:13][CH3:14])=[CH:7][CH:8]=2)[N:3]=1.[CH:16]([C:19]1[CH:23]=[CH:22][NH:21][N:20]=1)([CH3:18])[CH3:17]>>[OH:12][C:10]1[C:9]2[C:4](=[C:5]([CH3:15])[C:6]([O:13][CH3:14])=[CH:7][CH:8]=2)[N:3]=[C:2]([N:21]2[CH:22]=[CH:23][C:19]([CH:16]([CH3:18])[CH3:17])=[N:20]2)[N:11]=1

Participants

3

Reactant 2

HCID 178439403HCID 178439403, compoundHCID 1784877522-chloro-7-methoxy-8-methyl-1H-quinazolin-4-one

Product 1

HCID 1784877607-methoxy-8-methyl-2-(3-propan-2-ylpyrazol-1-yl)-1H-quinazolin-4-oneYield 63.4%

Conditions

Temperature
155 °C

Procedure

A mixture of 2-chloro-4-hydroxy-7-methoxy-8-methylquinazoline (140) (502 mg, 2.23 mmol) and 3-isopropylpyrazole (500 mg, 4.55 mmol) was heated at 155° C. for 10 min. Then, the reaction mixture was successively cooled down to room temperature, partitioned between CH2Cl2 and water, dried (Na2SO4) and evaporated. The residue was triturated in ether and filtered to give the title compound (422 mg, 63%) as white needles: m/z=299 (M+H)+.

Workup

  1. temperatureThen, the reaction mixture was successively cooled down to room temperature
  2. custompartitioned between CH2Cl2 and water
  3. dry with materialdried (Na2SO4)
  4. customevaporated
  5. customThe residue was triturated in ether
  6. filtrationfiltered

Sources & evidence

ORD record
ord-bbfde6ba36554b468815b89bebe5adab
Source dataset
uspto-grants-2010_02
Patent number
US07659245B2

Reaction notes

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