Methane → 2-(Methylthio)pyrazolo[1,5-a][1,3,5]triazin-4(3H)-one

HRID 1896083Notes

Reaction equation

[SH:1][C:2]1[N:7]=[C:6]([OH:8])[N:5]2[N:9]=[CH:10][CH:11]=[C:4]2[N:3]=1.[CH3:12]I.C>[OH-].[Na+]>[CH3:12][S:1][C:2]1[N:7]=[C:6]([OH:8])[N:5]2[N:9]=[CH:10][CH:11]=[C:4]2[N:3]=1

Participants

Conditions

Temperature: 5 °C

Procedure

Seven grams of 2-mercaptopyrazolo[1,5-a][1,3,5]triazin-4-ol (prepared according to the method described in Chemische Berichte, 1971, 104:3039-47) was dissolved in 5% aqueous NaOH (100 mL). The solution was cooled to 5° C. (ice bath) and 6 g. of methyl iodide was added dropwise. After 15-20 minutes, charcoal was added and the mixture was filtered then acidified with acetic acid. The precipitate (2-(methylthio)pyrazolo[1,5-a][1,3,5]triazin-4-ol was filtered, dried and isolated. Further recrystallization in AcOH gave 2-(methylthio)pyrazolo[1,5-a][1,3,5]triazin-4-ol. MS (ES+): 183.0 (M+1)+.

Workup

filtrationthe mixture was filtered
filtrationThe precipitate (2-(methylthio)pyrazolo[1,5-a][1,3,5]triazin-4-ol was filtered
customdried
customisolated
customFurther recrystallization in AcOH

Sources & evidence

ORD record: ord-e878e78a613846c587ff7347887e8f15
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08518931B2

Reaction notes

Loading…