Dimethylamine → N-[4,6-bis(dimethylamino)pyrimidin-5-yl]-cis-9-octadecenamide

HRID 2257193Notes

Reaction equation

HRID 2257193 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]=1

Participants

5

Reactant 4

HCID 674DimethylamineHCID 203124,6-Dichloro-5-nitropyrimidineHCID 5364783Oleoyl chlorideHCID 155853705-Amino-4,6-bis(dimethylamino)pyrimidine

Product 1

HCID 67710051N-[4,6-bis(dimethylamino)pyrimidin-5-yl]-cis-9-octadecenamide

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.

Sources & evidence

ORD record
ord-be407d4fdca044269584fc4279dafe36
Source dataset
uspto-grants-1997_08
Patent number
US05656634

Reaction notes

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