2,4-DIAMINO-PYRIMIDINE-5-CARBALDEHYDE

Yellow Solid

A solution of 0.41 g (2 mmol) of the compound of formula V was dissolved in methanol and 0.13 g (2 mmol) of Raney nickel (catalyst) was reacted with H2 at room temperature for 24 h, and an appropriate amount of water was added, extracted with ethyl acetate, The residue was purified by silica gel column chromatography (eluent: methanol: dichloromethane = 1: 30, v / v), and the residue was purified by silica gel column chromatography. To give a white solid (compound of formula V) in 81percent yield.Raney nickel (2.5 g of 50percent slurry with water) was added to a solution of 2, 4-diaminopyrimidine-5-carbonitrile (2.0 g, 14.8 mmol) in 98-100percent formic acid (20 mL) and the reaction mixture was refluxed for 3-4 h. After which, the reaction mixture was filtered and washed with 10 mL formic acid. The filtrate and washings were collected together and concentrated under reduced pressure. The resulting residue was stirred in 30percent ammonia solution and cooled to get free flowing solid product which was filtered and washed with water followed by drying to get of 2, 4-diaminopyrimidine- 5-carbaldehyde (1.8 g, yield: 78percent) as off white solid.General procedure: Vilsmeier reagent was prepared by mixing ice-cold dry DMF (50 ml) and POCl3 (30.0 mmol, 2.8 ml). The mixture was stirred for 15 min at 25 °C. To the previous mixture, aminopyrimidines (10.0 mmol) in dry DMF (5.0 ml) were added over a period of 15 min at 0-5 °C. The reaction mixturewas stirred for 24 h at 25 °C.The mixture was then added to cold, saturated aq. K2CO3 andextracted with diethyl ether. The organic layer was washed withwater, dried over anhydrous Na2SO4, and evaporated underreduced pressure to afford the crude product, whichwas purified ina silica gel column chromatography using hexane/ethyl acetate(9:1) as an eluent to give the title compounds 2 and 8. 4.3.1. 2, 4-Diaminopyrimidine-5-carbaldehyde (2) Brown powder, yield 59percent; 1H-NMR [DMSO-d6, 400 MHz]: (δ, ppm) 7.10 (d, 2H, NH2, exchange with D2O), 7.52 (d, 2H, NH2, exchangewith D2O), 8.32 (s, 1H, H6-pyrimidine), 9.45 (CHO); 13C NMR[DMSO-d6, 100 MHz]: (δ, ppm) 106.2 (C5-pyrimidine), 162.7(C4-pyrimidine), 164.4 (C6-pyrimidine), 167.0 (C2-pyrimidine), 189.5 (CHO).

Intermediate for the preparation of medicines and agrochemicals.

Molecular Weight:138.13
XLogP3:-0.5
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:5
Rotatable Bond Count:1
Exact Mass:138.05416083
Monoisotopic Mass:138.05416083
Topological Polar Surface Area:94.9
Heavy Atom Count:10
Complexity:129
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes