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

HRID 2379633Notes

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

Reactant 4

HCID 674Dimethylamine

HCID 203124,6-Dichloro-5-nitropyrimidine

HCID 5364783Oleoyl chloride

HCID 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-f229e4f9f6be46ad85a4bab66cb0f49e
Source dataset: uspto-grants-1994_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05362878

Reaction notes

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