1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 86685303, compound

HRID 1852969Notes

Reaction equation

[Cl:1][C:2]1[N:7]=[C:6]([C:8]2[CH:9]=[N:10][NH:11][CH:12]=2)[N:5]2[CH:13]=[CH:14][N:15]=[C:4]2[CH:3]=1.[CH:16]1([CH:19]=[CH:20][C:21]#[N:22])[CH2:18][CH2:17]1.C1CCN2C(=NCCC2)CC1>C(#N)C>[Cl:1][C:2]1[N:7]=[C:6]([C:8]2[CH:12]=[N:11][N:10]([CH:19]([CH:16]3[CH2:18][CH2:17]3)[CH2:20][C:21]#[N:22])[CH:9]=2)[N:5]2[CH:13]=[CH:14][N:15]=[C:4]2[CH:3]=1

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of 7-chloro-5-(1H-pyrazol-4-yl)imidazo[1,2-c]pyrimidine (0.107 g, 0.4872 mmol) and 3-cyclopropylacrylonitrile (Preparation B; 0.3403 g, 3.654 mmol) in 2 mL of acetonitrile was added DBU (0.1457 mL, 0.9744 mmol). The reaction mixture was sealed and heated to 50° C. and stirred overnight. To the reaction mixture was added more 3-cyclopropylacrylonitrile (0.100 g, 0.107 mmol) and DBU (0.072 mL, 0.448 mmol) and the reaction mixture was sealed and heated to 60° C. for 4 hours. The reaction mixture was loaded onto directly onto a column of silica gel and eluted with a gradient of 50-75% ethyl acetate in hexanes with 0.5% ammonium hydroxide to afford the title compound (0.119 g, 0.3729 mmol, 76.54% yield). MS (apci) m/z=313.1 (M+H).

Workup

customThe reaction mixture was sealed
customthe reaction mixture was sealed
temperatureheated to 60° C. for 4 hours
washeluted with a gradient of 50-75% ethyl acetate in hexanes with 0.5% ammonium hydroxide

Sources & evidence

ORD record: ord-a6d10353a66b43b681240b9d0022b434
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08962596B2

Reaction notes

Loading…