Hydrochloric Acid → N'-(2-Amino-4,6-dichloro-5-pyrimidinyl)-N,N-dimethylmethanimidamide
Reaction equation
[Cl:1][C:2]1[C:7]([N:8]=[CH:9][N:10]([CH3:12])[CH3:11])=[C:6]([Cl:13])[N:5]=[C:4]([N:14]=CN(C)C)[N:3]=1.Cl.CO.C(Cl)(Cl)Cl.[OH-].[NH4+]>C(O)C>[NH2:14][C:4]1[N:3]=[C:2]([Cl:1])[C:7]([N:8]=[CH:9][N:10]([CH3:11])[CH3:12])=[C:6]([Cl:13])[N:5]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
4,6-Dichloro-2,5-bis-{[(dimethylamino)methylene]amino}pyrimidine (Example 1, 5.87 g, 20.3 mmol) was dissolved in 95% ethanol (200 mL) and 6 N aqueous hydrochloric acid (13.5 mL) added. The solution was heated in an oil bath at 55° C. under nitrogen for 30 minutes, at which point TLC (silica gel, 5% methanol-chloroform) showed that starting material had been cleanly converted to a lower-Rf product. The cooled (ice bath) solution was adjusted to pH ~8 with concerned ammonium hydroxide and the resulting mixture (white precipitate formed) concentrated on a rotary evaporator to ~5 mL to remove ethanol. Additional water (20 mL) was added and the cooled mbiture was filtered. The white precipitate was washed with additional water (2×20 mL) and dried to give the title compound as a white powder (4.50 g, 95%), m.p. >dec 250° C.; mass spectrum (CI/CH4): 236, 234 (M+1); 1H-NMR (DMSO-d6)δ: 7.59 (s, 1, CH), 6.90 (s, 2, NH2), 3.00 and 2.94 (both s, 3 each, 2CH3); UV (pH 7 phosphate buffer) λmax: 328 nM (ε4500), 255 (15,800).
Workup
- temperatureThe cooled (ice bath) solution
- customthe resulting mixture (white precipitate formed)
- concentrationconcentrated on a rotary evaporator to ~5 mL
- customto remove ethanol
- additionAdditional water (20 mL) was added
- filtrationthe cooled mbiture was filtered
- washThe white precipitate was washed with additional water (2×20 mL)
- customdried
Sources & evidence
- ORD record
- ord-d1d19eb3e02747e8a6697149ee5025db
- Source dataset
- uspto-grants-2000_07
- Patent number
- US06087501
Reaction notes
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