Dimethylamine → N-[4,6-bis(dimethylamino)pyrimidin-5-yl]-cis-9-octadecenamide
Reaction equation
[NH2:1][C:2]1[C:3]([N:11]([CH3:13])[CH3:12])=[N:4][CH:5]=[N:6][C:7]=1[N:8]([CH3:10])[CH3:9].ClC1C([N+]([O-])=O)=C(Cl)N=CN=1.CNC.[C:28](Cl)(=[O:46])[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35]/[CH:36]=[CH:37]\[CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH3:45]>>[CH3:12][N:11]([CH3:13])[C:3]1[C:2]([NH:1][C:28](=[O:46])[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35]/[CH:36]=[CH:37]\[CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH3:45])=[C:7]([N:8]([CH3:9])[CH3:10])[N:6]=[CH:5][N:4]=1Participants
5
Procedure
5-Amino-4,6-bis(dimethylamino)pyrimidine (prepared by reacting commercially available 4,6-dichloro-5-nitro pyrimidine with excess dimethylamine followed by reduction of the nitro group according to the procedure of Jacobs et al., J. Am. Chem. Soc., 42, 2278 (1920)) was coupled with oleoyl chloride using the procedure described in Example 4 to give the title compound.