1-Methyl-5-(tributylstannyl)-3-(trifluoromethyl)-1H-pyrazole → 6-(4-methoxybenzyl)-8-vinylthieno[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-5(6H)-one

HRID 707461Notes

Reaction equation

Br[C:2]1[S:10][C:9]2[N:8]([CH2:11][C:12]3[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=3)[C:7](=[O:20])[N:6]3[N:21]=[CH:22][N:23]=[C:5]3[C:4]=2[CH:3]=1.CN1C([Sn](CCCC)(CCCC)CCCC)=[CH:28][C:27](C(F)(F)F)=N1>C1(C)C=CC=CC=1>[CH3:19][O:18][C:15]1[CH:16]=[CH:17][C:12]([CH2:11][N:8]2[C:9]3[S:10][C:2]([CH:27]=[CH2:28])=[CH:3][C:4]=3[C:5]3=[N:23][CH:22]=[N:21][N:6]3[C:7]2=[O:20])=[CH:13][CH:14]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a mixture of 8-bromo-6-(4-methoxybenzyl)thieno[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-5(6H)-one (80 mg, 0.20 mmol) in toluene (2 ml) was added 1-methyl-5-(tributylstannyl)-3-(trifluoromethyl)-1H-pyrazole (135 mg, 0.31 mmol). The resulting mixture was heated to 100° C. for 16 hours and cooled to room temperature. It was filtered through a pad of celite with DCM washing. The resulting filtrate was concentrated under reduced pressure, diluted in methanol, filtered and purified directly via reverse-phase HPLC to afford the title compound.

Workup

temperaturecooled to room temperature
filtrationIt was filtered through a pad of celite with DCM washing
concentrationThe resulting filtrate was concentrated under reduced pressure
additiondiluted in methanol
filtrationfiltered
custompurified directly via reverse-phase HPLC

Sources & evidence

ORD record: ord-de35e990dbb146d0b30844c0bd9fcf99
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09175010B2

Reaction notes

Loading…