Cyclopropylamine → 4-(Cyclopropylamino)-2-(methylthio)imidazo[2,1-f][1,2,4]triazine-7-carbonitrile

HRID 1430780Notes

Reaction equation

[CH:1]1([NH2:4])[CH2:3][CH2:2]1.[CH3:5][S:6][C:7]1[N:12]=[C:11](SC)[C:10]2=[N:15][CH:16]=[C:17]([C:18]#[N:19])[N:9]2[N:8]=1>C1COCC1>[CH:1]1([NH:4][C:11]2[C:10]3=[N:15][CH:16]=[C:17]([C:18]#[N:19])[N:9]3[N:8]=[C:7]([S:6][CH3:5])[N:12]=2)[CH2:3][CH2:2]1

Participants

Conditions

Temperature: 50 °C

Procedure

(I2B): Cyclopropanamine (2.69 mL, 42.4 mmol) was added to a suspension of 2,4-bis(methylthio)imidazo[2,1-f][1,2,4]triazine-7-carbonitrile (3.35 g, 14.12 mmol) in THF (30 mL) and the resulting mixture was heated at 50° C. overnight. Solvent was evaporated and the crude product was purified by flash chromatography on silica gel using an automated ISCO system (120 g column, eluting with 5-30% ethyl acetate/hexanes). 4-(cyclopropylamino)-2-(methylthio)imidazo[2,1-f][1,2,4]triazine-7-carbonitrile (3.39 g) was obtained as light yellow solid.

Workup

customSolvent was evaporated
customthe crude product was purified by flash chromatography on silica gel using
washan automated ISCO system (120 g column, eluting with 5-30% ethyl acetate/hexanes)

Sources & evidence

ORD record: ord-fe377c43d2fe49be9042838cbfa20a00
Source dataset: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08940736B2

Reaction notes

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