Methyl iodide → HCID 23287694, compound

HRID 367139Notes

Reaction equation

[C:1]([C:3]1[CH:20]=[CH:19][C:6]([NH:7][C:8]2[S:9][C:10]3[N:18]=[CH:17][CH:16]=[CH:15][C:11]=3[C:12](=[O:14])[N:13]=2)=[CH:5][CH:4]=1)#[N:2].[H-].[Li+].[CH3:23]I>>[C:1]([C:3]1[CH:20]=[CH:19][C:6]([N:7]=[C:8]2[N:13]([CH3:23])[C:12](=[O:14])[C:11]3[CH:15]=[CH:16][CH:17]=[N:18][C:10]=3[S:9]2)=[CH:5][CH:4]=1)#[N:2]

Participants

Reactant 3

HCID 6328Methyl iodide

HCID 62714Lithium hydride

HCID 23287603HCID 23287603, compound

Product 1

HCID 23287694HCID 23287694, compoundYield 80.7%

Procedure

The reaction procedure of Example 11 was followed except that 900 mg (3.21 mmol) of 2-(4-cyanoanilino)-4H-pyrido[3,2-e]-1,3-thiazin-4-one, 42 mg of lithium hydride and 547 mg of methyl iodide were used. The resulting residue was then purified through silica gel column chromatography (eluant: chloroform) to obtain 762 mg of 2-[(4-cyanophenyl)imino]-2,3-dihydro-3-methyl-4H-pyrido[3,2-e]-1,3-thiazin-4-one (81%, recrystallized from a mixture of ether and hexane).

Workup

customThe reaction procedure of Example 11
customThe resulting residue was then purified through silica gel column chromatography (eluant: chloroform)

Sources & evidence

ORD record: ord-4f3b3b0ba1784c908fb25b8807c20d63
Source dataset: uspto-grants-2000_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06133258

Reaction notes

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