2-Amino-5-pyrimidinecarboxyaldehyde

Light brown solid

Methyl 2-aminopyrimidine-5-carboxylate (300 mg, 2.0 mmol) was diluted in methanol (5 mL) containing a few drops of water. Lithium hydroxide (122 mg, 5.1 mmol) was added, and the reaction mixture was stirred at 60 °C overnight. The mixture was concentrated under reduced pressure, then diluted in water and adjusted to pH 4 with 1 M HCI. 2- Aminopyrimidine-5-carboxylic acid precipitated as a white solid, which was isolated by vacuum filtration (244 mg, 90percent): Vinamidinium salt (68, 158 g, 413 mmol) and guanidine hydrochloride (69, 63.3 g, 455 mmol) were dissolved in 527 mL of acetonitrile and cooled on an ice/water bath. Sodium hydroxide (66.1 mL, 50percent w/w, 827 mmol) was added dropwise, keeping the temperature below 25° C. The reaction was allowed to warm to 25° C. and stirred for 4 hours, then diluted with water and filtered, stripped from ethanol/heptane, then triturated with heptane. The resulting solid was dried under vacuum to provide the desired compound (70, 37 g, 301 mmol, 72.7percent yield).Preparation 3: Step 1: To a mixture of dialdehyde 19 (900 mg, 7.1 [MMOL)] and guanidine hydrochloride (678 mg, 7.1 [MMOL)] in absolute EtOH (20 ml) was added sodium ethoxide (483 mg, 7.1 [MMOL).] The reaction mixture was heated at 90 °C for 12 h, cooled to RT, concentrated-dry loaded on silica gel and flash chromatographed [(0-] 10percent [CH30H/20-30percent ACETONE/CH2CI2)] to produce 20 (355 mg, 2.9 mmol ; 41 percent) as a yellowish solid. Alternatively, 20 can be prepared according to the procedure described in JP Patent 63227573.To a mixture of 900 mg (7.1 mmol) of dialdehyde 66 and 678 mg (7.1 mmol) of guanidine hydrochloride in 20 mL of absolute ethanol was added 483 mg (7.1 mmol) of sodium ethoxide. Reaction mixture was heated at 90Sodium (1.2 g, 52 mmol) was dissolved in anhydrous ethanol (45 mL). To this freshly prepared solution was added methanetricarbaldehyde (14, 4.8 g, 47.96 mmol) and guanidine hydrochloride (5.5 g, 57.55 mmol). The resulting solution was stirred at room temperature for 1 hour and then refluxed for 20 hours. The solvent was evaporated and the residue was taken up in water (100 mL) and acidified to pH 1 by slow addition of 2N HCI. The acidic aqueous solution was neutralized by drop-wise addition of saturated aqueous sodium bicarbonate and was extracted by ethyl acetate (3 x 50 mL) Combined organic layers were washed with water, brine, dried over sodium sulfate andconcentrated under vacuo to afford 2-aminopyrimidine-5-carbaldehyde (15) as ayellowish solid. Yield: 2 g (34percent). 1H NMR (400 MHz, DMSO-d6) O 9.71 (5, 1H), 8.69 (5, 2H), 7.77 (br s, 2H). GCMS [mlz]: 123.0

Molecular Weight:123.11
XLogP3:-0.7
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:1
Exact Mass:123.043261792
Monoisotopic Mass:123.043261792
Topological Polar Surface Area:68.9
Heavy Atom Count:9
Complexity:98.4
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes