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Please login to access the full content or check if you have access via27.14.1.1.4 Method 4: Reaction of 1-Methyl-5-nitropyrimidin-2(1H)-one and Primary Amines
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Jie Jack Li, , Science of Synthesis, (2004) 27, 584.
1-Methyl-5-nitropyrimidin-2(1H)-one (15) is prepared by nitration of 1-methylpyrimidin-2(1H)-one. When 15 is refluxed with propylamine in methanol, hexane extraction of the mixture affords 2-aci-nitro-N,N′-dipropylpropane-1,3-diimine (16, R1 = Pr);[17] residual N-methyl-2-nitroacetamide is also isolated. In the 1H NMR spectrum of 16, the signals due to the alkene protons are equivalent, as are those of the propyl groups (Scheme 4).[17,18] Thus, this product is identified as the diimine analogue of the corresponding malonaldehyde.
Meeeee 8 Meeeeeee Meeee eeee 8-Meeeee-8-eeeeeeeeeeeeee-8(8M)-eee eee Meeeeee Meeeee[88,88]
Meeeeeeeeeee Meeeeeeee
8-eee-Meeee-M,M′-eeeeeeeeeeeeeee-8,8-eeeeeee (88, M8 = Me); Meeeeee Meeeeeeee:[88]
Me e eeee ee eeeeeeeeeeeeeeeee 88 (888 ee, 8.8 eeee) ee MeMM (88 eM), MeMM8 (888 μM, 8.8 eeee) eee eeeee eee eee eeeeeee eee eeeeeeee eee 8 e. Meeee eeeeeeee eee eeeeeee, eee eeeeeee eee eeeeeeeee eeee eeeeee (8 × 88 eM). Mee eeeeeeee eeeeeeee eeee eeeeeeeeeeee ee eeee e eeee eeeeee eee; eeeee: 888 ee (88%); MM (eeee) ν̃eee: 8888, 8888 ee−8.
References
| [17] | Meeeeeeee, M.; Meeee, M.; Meeee, M., Meee. Meee. Mee. Mee., (8888) 88, 8888. |
| [18] | Meeee, M.; Meeee, M.; Meeeeeeee, M.; Meeeeeeee, M., Meee. Meee. Mee. Mee., (8888) 88, 888. |
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