Methyl iodide → HCID 15702783, compound

HRID 2073195Notes

Reaction equation

[NH2:1][C:2]([C:4]1[CH:5]=[N:6][N:7]2[C:12]([C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([F:22])([F:21])[F:20])[CH:14]=3)=[CH:11][CH2:10][N:9]([C:23]([NH:25][C:26](=[O:30])[O:27][CH2:28][CH3:29])=S)[C:8]=12)=[O:3].[H-].[Na+].CI>O1CCCC1>[O:3]=[C:2]1[N:1]=[C:23]([NH:25][C:26](=[O:30])[O:27][CH2:28][CH3:29])[N:9]2[C:8]3[N:7]([C:12]([C:13]4[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([F:22])([F:21])[F:20])[CH:14]=4)=[CH:11][CH2:10]2)[N:6]=[CH:5][C:4]1=3

Participants

Conditions

Temperature: 0 °C

Procedure

To a stirred solution of 300 mg of [[3-(amino carbonyl)-7-[3-(trifluoromethyl)phenyl]pyrazolo[1,5-a]pyrimidin-4(5H)-yl]-thioxomethyl]carbamic acid, ethyl ester (Example 12) in 15.0 ml of dry tetrahydrofuran cooled in an ice bath at 0° C. was added 30 mg of sodium hydride (60% dispersion in mineral oil) in one portion. After the evolution of gas ceased the mixture was stirred for an additional 30 minutes at 0° C., then 1.0 ml of methyl iodide was added and the reaction mixture was allowed to warm to room temperature with stirring for 2 hours. The mixture was quenched with water and diluted in water. The aqueous solution was extracted with chloroform. The chloroform extracts were combined and evaporated in vacuo and the residue was triturated with ether. The solid was collected by filtration to give the desired product as a white solid, m.p. 219°-220° C.

Workup

temperatureto warm to room temperature
stirringwith stirring for 2 hours
customThe mixture was quenched with water
additiondiluted in water
extractionThe aqueous solution was extracted with chloroform
customevaporated in vacuo
customthe residue was triturated with ether
filtrationThe solid was collected by filtration

Sources & evidence

ORD record: ord-361bc36a235d45d990f49b78936cdb9c
Source dataset: uspto-grants-1990_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04916137

Reaction notes

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