2(1H)-Pyrimidinone,hydrazone(9CI)

A mixture of 2-chloropyrimidine (15 g, 131 mmol), NH2NH2.H2O (30 ml), K2CO3 (15 g, 109 mmol) was stirred at 100 °C for 30 min. The mixture was ice cooled and the resulting crude crystals were collected by filtration. The crystals were washed with cold water, air dried, and recrystallized from petroleum ether (150 ml) to give compound 350a (14.4 g, 131 mmol, yield: 99.8percent) as a yellow solid. 1H NMR (400mhz, DMSO-d6) δ 8.30 (d, = 4.8 hz, 2h), 8.12 (br s, ih), 6.59 (t, j = 4.7 hz, ih), 4.13 (s, 2h).H2mphp was synthesized by the following procedure. 2-Chloropyrimidine (1.145 g, 20 mmol) was dissolvedin ethanol (30 mL). Then, excess hydrazine hydrate (85percent, 6 mL) was added to the above solutionunder stirring. A bright yellow solution formed, from which white needle crystals appeared after 2 h. The crystals were collected by filtration and recrystallized in ethanol (yield 80percent). 3-Methylsalicylaldehyde(1.36 g, 10 mmol) was added to an ethanolic solution (30 mL) of 2-hydrazinopyrimidine (1.10 g, 10 mmol)and light yellow precipitate formed immediately. After reflux for 3 h, the reaction mixture was filteredand the precipitate washed with ethanol to yield light yellow powder of H2mphp. Yield 95percent.[Referential Example 34] 2-Hydrazinopyrimidine; Hydrazine monohydrate (20 ml) was added to a suspension of 2-chloropyrimidine (6.00 g) in ethanol (60 ml) at room temperature, and the mixture was stirred for 80 minutes. The solvent was evaporated under reduced pressure, and water (34 ml) was added to the residue. The solid precipitate was collected by filtration to give the title compound (2.30 g, 40percent). [Referential Example 3] 2-Hydrazinopyrimidine Hydrazine monohydrate (20 mL) was added to a suspension of 2-chloropyrimidine (6.00 g) in ethanol (60 mL) at room temperature, followed by stirring for 80 minutes. The solvent of reaction mixture was evaporated under reduced pressure, and then water (34 mL) was added to the residue. The solid that precipitated was collected through filtration, to thereby give the title compound (2.30 g, 40percent). PREPARATION 9Preparation of 2-hydrazinylpyrimidine; A solution of 2-chloropyrimidine (0.70 g, 6.11 mmol) in pyridine (15 mL) and anhydrous hydrazine (2.5 mL) was stirred for 5 minutes at ambient temperature, and further pyridine (8 mL) was added. The reaction mixture was stirred at ambient temperature for 1.5 h and concentrated in vacuo. The residue was suspended in water (4 mL) and the resultant solid was collected by suction filtration and air-dried to afford 2-hydrazinylpyrimidine as a colorless solid in 25percent yield (0.171 g): Dissolve 2-chloropyrimidine (10.04 g, 87.7 mmol) in pyridine (200 mL) and add hydrazine (35.8 mL, 1.14 mol) to the mixture followed by pyridine (100 mL). Stir the mixture for 3 hr. at room temperature then concentrate. Suspend the residue in water and filter. Wash the cake with cold methanol. Collect the powder and dry under vacuum to give pyrimidin-2-ylhydrazine as a white powder (8.05 g, 83percent).

Molecular Weight:110.12
XLogP3:-0.2
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:1
Exact Mass:110.059246208
Monoisotopic Mass:110.059246208
Topological Polar Surface Area:63.8
Heavy Atom Count:8
Complexity:59.1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes