Dimethylformamide → HCID 86737689, compound

HRID 443850Notes

Reaction equation

[CH3:1][O:2][C:3]1[C:4]([O:20][CH3:21])=[CH:5][C:6]2[C:7](=[O:19])[N:8]3[N:15]=[C:14]([C:16]([OH:18])=[O:17])[CH:13]=C3NC=2[CH:12]=1.[C:22](=O)([O-])[O-].[K+].[K+].CI.[CH3:30][N:31]([CH:33]=O)[CH3:32]>>[CH3:1][O:2][C:3]1[C:4]([O:20][CH3:21])=[CH:5][C:6]2[C:7](=[O:19])[N:8]3[N:15]=[C:14]([C:16]([O:18][CH3:22])=[O:17])[CH:13]=[C:33]3[N:31]([CH3:30])[C:32]=2[CH:12]=1

Participants

Reactant 4

HCID 6228Dimethylformamide

HCID 6328Methyl iodide

HCID 11430Potassium Carbonate

HCID 178486890HCID 178486890, compound

Product 1

HCID 86737689HCID 86737689, compound

Procedure

From 4,9-dihydro-6,7-dimethoxy-9-oxo-pyrazolo[5,1-b]-quinazoline-2-carboxylic acid (1.5 g; 5.2 mmole), anhydrous potassium carbonate (3.0 g; 22 mmole), methyl iodide (15 ml) and DMF (50 ml), following the procedure of Example 11, there is obtained 4,9-dihydro-6,7-dimethoxy-4-methyl-9-oxo-pyrazolo[5,1-b]quinazoline-2-carboxylic acid, methyl ester (1.8 g); mp 301°-303° (d). The crude methyl ester (1.8 g) is hydrolyzed with 1(N) sodium hydroxide solution (50 ml) as in Example 11 to give 4,9-dihydro-6,7-dimethoxy-4-methyl-9-oxo-pyrazolo-[5,1-b]quinazoline-2-carboxylic acid (0.95 g) mp 284°-5° (d), after crystallization from DMF/methanol.

Sources & evidence

ORD record: ord-cf861c2d9e1c4b4ea707148354819c2a
Source dataset: uspto-grants-1981_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04261997

Reaction notes

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