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CAS No. : | 16462-27-4 | MDL No. : | MFCD00085600 |
Formula : | C5H5N5 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | OYUQCQCQLDTRHQ-UHFFFAOYSA-N |
M.W : | 135.13 | Pubchem ID : | 282115 |
Synonyms : |
|
Num. heavy atoms : | 10 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 0 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 2.0 |
Molar Refractivity : | 35.56 |
TPSA : | 101.61 Ų |
GI absorption : | High |
BBB permeant : | No |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -7.28 cm/s |
Log Po/w (iLOGP) : | 0.61 |
Log Po/w (XLOGP3) : | -0.22 |
Log Po/w (WLOGP) : | -0.47 |
Log Po/w (MLOGP) : | -1.82 |
Log Po/w (SILICOS-IT) : | -0.52 |
Consensus Log Po/w : | -0.48 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -0.98 |
Solubility : | 14.0 mg/ml ; 0.104 mol/l |
Class : | Very soluble |
Log S (Ali) : | -1.46 |
Solubility : | 4.72 mg/ml ; 0.0349 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -0.99 |
Solubility : | 13.9 mg/ml ; 0.103 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.93 |
Signal Word: | Warning | Class: | |
Precautionary Statements: | P280-P305+P351+P338 | UN#: | |
Hazard Statements: | H317-H319 | Packing Group: | |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | With hydrogen In methanol at 20℃; for 24 h; | 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. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | With Raney Nickel In water for 3 - 4 h; Reflux | 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. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
71% | With sodium ethanolate In ethanol at 5℃; for 8 h; | 1.22 g (10 mmol) of guanidine nitrate was dissolved in 50 ml of sodium ethoxide and ethanol, and 1.22 g (10 mmol) of ethoxymethylenemalonitrile was added at 5 ° C for 8 h. Appropriate amount of water was added and extracted with ethyl acetate The organic phase was washed with saturated brine and the organic phase was concentrated (the solvent was removed under reduced pressure). The residue was purified by silica gel column chromatography (eluent: dichloromethane = 1: 30, v / v) to give a white solid (compound of formula IV) in 71percent yield. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
79% | Stage #1: for 0.166667 - 0.25 h; Reflux Stage #2: at 20℃; for 8 h; |
To the freshly prepared sodium ethoxide [sodium (0.83 g, 36 mmol) in 20 ml absolute ethanol] solution; guanidine hydrochloride (3.1 g, 32.8 mmol) was added and the reaction mixture was heated to reflux for 10-15 min, the clear solution immediately turned turbid white. The solution was filtered and washed with 10 mL absolute ethanol and the filtrate with combined washings was used further. To the filtrate, ethoxymethylene malononitrile (4 g, 32.8 mmol) was added in portions and the reaction mixture stirred for 8 h at room temperature, after which it was concentrated to dryness and the obtained residue was dissolved in glacial acetic acid at reflux temperature. On cooling yellow crystals started precipitating out. The product was filtered, washed with diethyl ether (2x20mL) and then dried to yield of 2, 4-diaminopyrimidine-5-carbonitrile (3.5 g, 79percent) as yellow solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
66% | With hydrogenchloride; sodium bicarbonate In water; acetic acid; acetone | 2,4-Diamino-5-(3,5-diethyl-4-hydroxybenzyl)pyrimidine 2,4-Diamino-5-hydroxymethyl pyrimidine (1.4 g. 0.01 mole) and 2,6-diethylphenol (1.6 g., 0.01 mole) in glacial acetic acid (100 ml) containing conc. hydrochloric acid (3 ml.), were heated on a steam-bath. The initial precipitate slowly dissolved After 5 hours the reaction was cooled and evaporated to dryness on a rotary-evaporator. The residue was treated with acetone (50 ml.) and triturated to give a granular solid. The solid was filtered and recrystallized from water to give the product as the hydrochloride, m.p. 277°-279° C. Alternatively, the crude solid or the hydrochloride was dissolved in hot water and neutralised with a solution of sodium hydrogen carbonate to give the free base. Recrystallisation from aqueous ethanol gave colourless needles of 2,4-diamino-5-(3,5-diethyl-4-hydroxybenzyl)pyrimidine, m.p. 204°-205° C. Yield 66percent on theory. |
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