Iodine → 8-Iodo-1,4,4-trimethyl-4,5-dihydro-1h-pyrazolo[4,3-h]quinazoline-3-carboxylic acid methylamide

HRID 44633

Reaction equation

[CH3:1][NH:2][C:3]([C:5]1[C:9]2[C:10]([CH3:22])([CH3:21])[CH:11](CC)[C:12]3[CH:13]=[N:14][C:15](N)=[N:16][C:17]=3[C:8]=2[N:7]([CH3:23])[N:6]=1)=[O:4].[I-:24].[Cs+].II.N(OCCC(C)C)=O>[Cu]I.C(COC)OC>[CH3:1][NH:2][C:3]([C:5]1[C:9]2[C:10]([CH3:22])([CH3:21])[CH2:11][C:12]3[CH:13]=[N:14][C:15]([I:24])=[N:16][C:17]=3[C:8]=2[N:7]([CH3:23])[N:6]=1)=[O:4]

Participants

Conditions

Temperature: 70 °C

Procedure

In a round bottom flask maintained under argon atmosphere, ethyl 8-amino-1,4,4-trimethyl-4,5-dihydro-1H-pyrazolo[4,3-h]quinazoline-3-carboxylic acid methylamide (13.00 g, 45.400 mmol) was dissolved into anhydrous dimethoxyethane (800 mL); cesium iodide (11.795 g, 45.400 mmol), bisublimated iodine (5.761 g, 22.698 mmol), copper(I) iodide (2.594 g, 13.621 mmol), and iso-amyl nitrite (9.107 mL, 68.100 mmol) were added in that order and the mixture was heated to 70° C. for 22 hours.

Workup

temperatureIn a round bottom flask maintained under argon atmosphere

Sources & evidence

ORD record: ord-1712e10069594564bdddcc990bb7193f
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08541429B2

Linked notes

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