Dimethyl Sulfoxide → 5-Pyrimidinecarbonitrile, 2-amino-4-(1,3-benzodioxol-5-yl)-6-(methylthio)-

HRID 1355712Notes

Reaction equation

HRID 1355712 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10](=O)[CH2:11][C:12]#[N:13])=[CH:9][C:4]=2[O:3][CH2:2]1.[H-].[Na+].CI.[N+]([O-])(O)=O.[NH2:23][C:24]([NH2:26])=[NH:25].[CH3:27][S:28]([CH3:30])=O>CN(C=O)C.C(N(CC)CC)C.C(=S)=S>[NH2:25][C:24]1[N:26]=[C:10]([C:8]2[CH:7]=[CH:6][C:5]3[O:1][CH2:2][O:3][C:4]=3[CH:9]=2)[C:11]([C:12]#[N:13])=[C:27]([S:28][CH3:30])[N:23]=1

Participants

9

Reactant 5

HCID 679Dimethyl SulfoxideHCID 6328Methyl iodideHCID 10481Guanidine NitrateHCID 24758Sodium hydrideHCID 196165383-(2H-1,3-Benzodioxol-5-yl)-3-oxopropanenitrile

Product 1

HCID 185073005-Pyrimidinecarbonitrile, 2-amino-4-(1,3-benzodioxol-5-yl)-6-(methylthio)-

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 6348Carbon DisulfideSolventHCID 8471TriethylamineSolvent

Procedure

From 3-benzo[1,3]dioxol-5-yl-3-oxo-propionitrile with sodium hydride, carbon disulphide and methyl iodide in DMSO. Then treatment with guanidine nitrate and triethylamine in DMF. EI-MS m/e (%):286 (M+, 96), 285 ([M—H]+, 100).

Sources & evidence

ORD record
ord-f949db601a094752ac13f823f030f5f5
Source dataset
uspto-grants-2003_07
Patent number
US06586441B2

Reaction notes

Loading…