* 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.
Reference：
[1] Yakugaku Zasshi, 1937, vol. 57, p. 579,581; dtsch. Ref. S. 109, 111[2] Chem.Abstr., 1937, p. 6238
3
[ 6622-92-0 ]
[ 4472-45-1 ]
Yield
Reaction Conditions
Operation in experiment
82%
With trichlorophosphate In toluene for 3 h; Reflux
POCl3 (0.460 g, 3.0 mmol) was added to the solution of compound 13 (1.0 mmol) in 15 mL of toluene and the mixture was stirred at reflux for 3 hours. Redundant POCl3 was removed under reduced pressure and ice water (10mL) was added. The solution was adjusted to the pH 9-10 with sodium carbonate and then extracted with methyl tert-butyl ether (MTBE). The organic phase was dried over sodium sulfate, and the solvent was removed under reduced pressure to afford compound 14. (Yield: 82percent) MS (ESI) (m /z) [M+H]+ 143.1.
71%
With ammonia In sodium chloride; dichloromethane; trichlorophosphate
Part 1 Preparation of 2,4-dimethyl-6-chloropyrimidine. METHOD: 20 g (16.1*10-2 mol) of 2,4-dimethyl-6-hydroxypyrimidine in suspension in 150 ml of phosphorus oxychloride are introduced into a 250 ml three-necked flask fitted with a thermometer, a condenser and a magnetic stirrer. The mixture is heated at 90° C. for one and a half hours. The mixture is then cooled and then evaporated to dryness. The residue which crystallises at ambient temperature is added, in small portions, to a binary mixture consisting of dichloromethane (200 ml) and 10percent ammonia (300 ml), previously cooled to -5° C. in an ice bath containing sodium chloride. The mixture is stirred cold for half an hour and the organic phase is then decanted off, washed with water until neutral and then dried over sodium sulphate, filtered and evaporated. The yellow liquid obtained is filtered through a glass frit filled with silica using the dichloromethane/methanol (99/1) eluent system; the pure fractions collected are evaporated. 16.4 g of a colourless liquid which has a persistent odour and which crystallises in a refrigerator are obtained. Yield: 71percent. Elementary analysis for C6 H7 ClN2; molecular weight=142.5. The 1 H and 13 C NMR and mass spectra are in accordance with the expected structure.
Reference：
[1] Bioorganic and Medicinal Chemistry Letters, 2018, vol. 28, # 10, p. 1769 - 1775
[2] Tetrahedron Letters, 1999, vol. 40, # 42, p. 7477 - 7478
[3] Patent: US5438058, 1995, A,
[4] Patent: US6093718, 2000, A,
4
[ 6622-92-0 ]
[ 4472-45-1 ]
Reference：
[1] Heterocycles, 2006, vol. 68, # 9, p. 1973 - 1979
[2] Helvetica Chimica Acta, 2001, vol. 84, # 5, p. 1112 - 1118
[3] Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 22, p. 6439 - 6442
5
[ 6622-92-0 ]
[ 10025-87-3 ]
[ 4472-45-1 ]
Reference：
[1] Chemische Berichte, 1902, vol. 35, p. 1577
6
[ 124-42-5 ]
[ 141-97-9 ]
[ 6622-92-0 ]
Yield
Reaction Conditions
Operation in experiment
36%
With sodium ethanolate In ethanol for 20 h; Reflux
2,6-dimethylpyrimidin-4-ol. Ethyl 3-oxobutanoate (10.0 g, 77 mmol) and acetimidamide hydrochloride (7.23 g, 77 mmol) were added to the solution of sodium ethanolate (10.5 g, 154 mmol) in ethanol (200 mL). And the mixture was refluxed for 20 hours. Water (10 mL) was added to the mixture. The resultant mixture was concentrated to give a residue. The residue was purified by column chromatography (silica gel, dichloromethane /methanol = 15: 1) to give 2,6-dimethylpyrimidin-4-ol as a yellow solid (3.43 g, 36percent). LRMS (M + H+) m/z: calcd 124.06; found 124.
29%
With potassium carbonate In water at 20℃; for 0.25 h; Microwave irradiation
General procedure: The corresponding amidine hydrochloride (2.54 mmol) and powdered K2CO3 (5.76 mmol) were dissolved in water (5.0 mL) in a 20-mL vessel. The β-keto ester (2.31 mmol) was added and the resulting mixture was irradiated for 5–15 min (see Table 2). Upon the end of the reaction (TLC, hexanes/EtOAc, 5:1), the mixture was diluted with sat. aq NH4Cl (5.0 mL) and extracted with CH2Cl2 (3 × 15 mL). The combined organic phases were dried (anhyd Na2SO4) and filtered. The filtrate was rotary evaporated and the obtained crude product was purified by column chromatography [silica gel, hexane/EtOAc mixtures or recrystallized (EtOH)].
With sodium ethanolate In ethanol for 20 h; Reflux
Ethyl 3-oxobutanoate (10.0 g, 77 mmol) and acetimidamide hydrochloride (7.23 g, 77 mmol) were added to the solution of sodium ethanolate (10.5 g, 154 mmol) in ethanol(200 mE). And the mixture was refluxed for 20 hours. Water (10 mE) was added to the mixture. The resultant mixture wasconcentrated to give a residue. The residue was purified bycolunm chromatography (silica gel, dichloromethane/methanol=1 5:1) to give 2,6-dimethylpyrimidin-4-ol as a yellowsolid (3.43 g, 36percent). ERMS (M+H) mlz: calcd 124.06. found124.
With iodine; sodium hydroxide In water at 80℃; for 2 h;
Step A: 2,6-Dimethylpyrimidin-4-ol (5.0 g, 40 mmol) was dissolved in aqueous NaOH solution (50 mL, 1 M, 50 mmol). To the solution was added iodine (10.2 g, 40 mmol). The mixture was gradually heated to 80° C. and stirred for 2 h. After cooling the mixture to room temperature, acetic acid was added to adjust the pH ˜6. A precipitate formed and was collected by filtration. The solid was washed with water and dried to give 5-iodo-2,6-dimethylpyrimidin-4-ol (6.51 g, 65percent). MS m/z 251.2 [M+H]+.
Reference：
[1] Patent: US9617268, 2017, B2, . Location in patent: Page/Page column 398
[2] Journal of Medicinal Chemistry, 1998, vol. 41, # 22, p. 4251 - 4260
[3] Tetrahedron, 2007, vol. 63, # 9, p. 1931 - 1936
[4] Patent: US5466692, 1995, A,
[5] Patent: US2012/95031, 2012, A1, . Location in patent: Page/Page column 160
(E)-4-[2-(4-hydroxy-6-methyl-pyrimidin-2-yl)-vinyl]-benzonitrile[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
90%
In acetic anhydride;
b) In analogy to example 12b), from <strong>[6622-92-0]2,4-dimethyl-6-hydroxypyrimidine</strong> (1.24 g, 10 mmol) and 4-cyanobenzaldehyde (1.31 g, 10 mmol) in acetic anhydride there was obtained (E)-4-[2-(4-hydroxy-6-methyl-pyrimidin-2-yl)-vinyl]-benzonitrile (2.13 g, 90%) as a light yellow solid. EI mass spectrum, m/e: 237.1 (M calculated for C14H11N3O: 237).
(E)-2-[2-(3-methoxy-phenyl)-vinyl]-6-methyl-pyrimidin-4-ol[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
29%
In acetic anhydride;
b) In analogy to example 12b), from <strong>[6622-92-0]2,4-dimethyl-6-hydroxypyrimidine</strong> (1.5 g, 12 mmol) and 3-methoxybenzaldehyde (1.6 g, 12 mmol) in acetic anhydride there was obtained (E)-2-[2-(3-methoxy-phenyl)-vinyl]-6-methyl-pyrimidin-4-ol (0.84 g, 29%) as a yellow solid. EI mass spectrum, m/e: 242 (M calculated for C14H14N2O2: 242).
(E)-6-methyl-2-[2-(3-fluoro-phenyl)-vinyl]-pyrimidin-4-ol[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
53%
In acetic anhydride;
b) In analogy to example 12b), from <strong>[6622-92-0]2,4-dimethyl-6-hydroxypyrimidine</strong> (1.24 g, 10 mmol) and 3-fluorobenzaldehyde (1.24 g, 10 mmol) in acetic anhydride there was obtained (E)-6-methyl-2-[2-(3-fluoro-phenyl)-vinyl]-pyrimidin-4-ol (1.22 g, 53%) as a light-yellow solid. EI mass spectrum, m/e: 230.1 (M calculated for C13H11FN2O: 230).
(E)-2-[2-(3-chloro-phenyl)-vinyl]-6-methyl-pyrimidin-4-ol[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
1.92 g (78%)
In acetic anhydride;
b) 1.24 g (10 mmol) of <strong>[6622-92-0]2,4-dimethyl-6-hydroxypyrimidine</strong> in acetic anhydride (2.8 ml) were treated at RT with 1.41 g (10 mmol) of 3-chlorobenzaldehyde and the mixture was heated for 5 hours at 145 C. until completion of the reaction according to TLC analysis. The reaction mixture was cooled to RT, the crystalline solid which had formed was filtered off by suction and washed with diethyl ether to give 1.92 g (78%) of the desired (E)-2-[2-(3-chloro-phenyl)-vinyl]-6-methyl-pyrimidin-4-ol as off-white crystals. EI mass spectrum, m/e: 246.1 (M calculated for C13H11ClN2O: 246).
(E)-3-[2-(4-hydroxy-6-methyl-pyrimidin-2-yl)-vinyl]-benzonitrile[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
74%
In acetic anhydride;
b) In analogy to example 12b), from <strong>[6622-92-0]2,4-dimethyl-6-hydroxypyrimidine</strong> (1.1 g, 8.86 mmol) and 3-cyanobenzaldehyde (1.16 g, 8.86 mmol) in acetic anhydride there was obtained (E)-3-[2-(4-hydroxy-6-methyl-pyrimidin-2-yl)-vinyl]-benzonitrile (1.56 g, 74%) as a yellow solid. EI mass spectrum, m/e: 237 (M calculated for C14H11N3O: 237).
(E)-3-[2-(4-hydroxy-6-methyl-pyrimidin-2-yl)-vinyl]-benzoic acid methyl ester[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
78%
In acetic anhydride;
b) In analogy to example 12b), from <strong>[6622-92-0]2,4-dimethyl-6-hydroxypyrimidine</strong> (1.86 g, 15 mmol) and 3-methoxycarbonylbenzaldehyde (2.46 g, 15 mmol) in acetic anhydride there was obtained (E)-3-[2-(4-hydroxy-6-methyl-pyrimidin-2-yl)-vinyl]-benzoic acid methyl ester (3.16 g, 78%) as a yellow solid. ISN mass spectrum, m/e: 269.3 (M-H calculated for C15H14N2O3: 269).
(E)-2-[2-(4-dimethylamino-phenyl)-vinyl]-6-methyl-pyrimidin-4-ol[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
In acetic anhydride;
b) In analogy to example 12b), from <strong>[6622-92-0]2,4-dimethyl-6-hydroxypyrimidine</strong> (1.5 g, 12 mmol) and 4-dimethylaminobenzaldehyde (1.8 g, 12 mmol) in acetic anhydride there was obtained (E)-2-[2-(4-dimethylamino-phenyl)-vinyl]-6-methyl-pyrimidin-4-ol (3.1 g) as a black oil which was used in the next reaction without further purification.
(E)-2-[2-(2,4-dichloro-phenyl)-vinyl]-6-methyl-pyrimidin-4-ol[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
74%
In acetic anhydride;
b) In analogy to example 12b), from <strong>[6622-92-0]2,4-dimethyl-6-hydroxypyrimidine</strong> (1.24 g, 10 mmol) and 2,4-dichlorobenzaldehyde (1.75 g, 10 mmol) in acetic anhydride there was obtained (E)-2-[2-(2,4-dichloro-phenyl)-vinyl]-6-methyl-pyrimidin-4-ol (2.08 g, 74%) as a light yellow solid. EI mass spectrum, m/e: 280 (M calculated for C13H10Cl2N2O: 280).
(E)-6-methyl-2-(2-thiophen-2-yl-vinyl)-pyrimidin-4-ol[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
23%
In acetic anhydride;
b) In analogy to example 12b), from <strong>[6622-92-0]2,4-dimethyl-6-hydroxypyrimidine</strong> (1.24 g, 10 mmol) and 2-thiphenecarboxaldeyde (1.12 g, 10 mmol) in acetic anhydride there was obtained (E)-6-methyl-2-(2-thiophen-2-yl-vinyl)-pyrimidin-4-ol (0.51 g, 23%) as a yellow solid. EI mass spectrum, m/e: 218.1 (M calculated for C11H10N2OS: 218).
(E)-2-(2-benzo[1,3]dioxol-5-yl-vinyl)-6-methyl-pyrimidin-4-ol[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
24.5%
In acetic anhydride;
b) In analogy to example 12b), from <strong>[6622-92-0]2,4-dimethyl-6-hydroxypyrimidine</strong> (1.5 g, 12 mmol) and piperonal (1.8 g, 12 mmol) in acetic anhydride there was obtained (E)-2-(2-benzo[1,3]dioxol-5-yl-vinyl)-6-methyl-pyrimidin-4-ol (0.76 g, 24.5%) as a yellow solid. EI mass spectrum, m/e: 256 (M calculated for C14H14N2O3: 256).
(E)-2-[2-(3-benzyloxy-phenyl)-vinyl]-6-methyl-pyrimidin-4-ol[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
54%
In acetic anhydride;
b) In analogy to example 12b), from <strong>[6622-92-0]2,4-dimethyl-6-hydroxypyrimidine</strong> (2 g, 16.1 mmol) and 3-benzyloxybenzaldehyde (3.42 g, 16.1 mmol) in acetic anhydride there was obtained (E)-2-[2-(3-benzyloxy-phenyl)-vinyl]-6-methyl-pyrimidin-4-ol (2.8 g, 54%) as a off-white solid. EI mass spectrum, m/e: 318 (M calculated for C20H18N2O2: 318).
(E)-2-[2-(2,4-dimethoxy-phenyl)-vinyl]-6-methyl-pyrimidin-4-ol[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
21%
In acetic anhydride;
b) In analogy to example 12b), from <strong>[6622-92-0]2,4-dimethyl-6-hydroxypyrimidine</strong> (1.86 g, 15 mmol) and 2,4-dimethoxybenzaldehyde (2.7 g, 15 mmol) in acetic anhydride there was obtained (E)-2-[2-(2,4-dimethoxy-phenyl)-vinyl]-6-methyl-pyrimidin-4-ol (0.864 g, 21%) as a yellow solid. EI mass spectrum, m/e: 272.1 (M calculated for C15H16N2O3: 272).
2-[2-(3,5-dichloro-phenyl)-vinyl]-6-methyl-pyrimidin-4-ol[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
93%
In acetic anhydride;
b) In analogy to example 12b), from <strong>[6622-92-0]2,4-dimethyl-6-hydroxypyrimidine</strong> (2 g, 16.1 mmol) and 3,5-dichloro-benzaldehyde (2.8 g, 16 mmol) in acetic anhydride there was obtained 2-[2-(3,5-dichloro-phenyl)-vinyl]-6-methyl-pyrimidin-4-ol (4.24 g, 93%) as an light-red solid. ISP mass spectrum, m/e: 281.1 (M+1 calculated for C13H10Cl2N2O: 281).
(E)-2-[2-(4-methoxy-phenyl)-vinyl]-6-methyl-pyrimidin-4-ol[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
12.5%
In acetic anhydride;
b) In analogy to example 12b), from <strong>[6622-92-0]2,4-dimethyl-6-hydroxypyrimidine</strong> (1.24 g, 10 mmol) and 4-methoxybenzaldehyde (1.36 g, 10 mmol) in acetic anhydride there was obtained (E)-2-[2-(4-methoxy-phenyl)-vinyl]-6-methyl-pyrimidin-4-ol (0.304 g, 12.5%) as a yellow solid. EI mass spectrum, m/e: 242.1 (M calculated for C14H14N2O2: 242).
methyl α-(2-bromomethylphenyl)-β-methylacrylate[ No CAS ]
[ 6622-92-0 ]
[ 145910-14-1 ]
Yield
Reaction Conditions
Operation in experiment
With potassium carbonate; In N-methyl-acetamide; water;
EXAMPLE 16 Preparation of methyl alpha-[2-(2',6'-dimethyl-4'-pyrimidinyl)-oxymethylphenyl]-beta-methylacrylate (compound 6) STR113 2.05 g (16.5 mmol; 10% excess) of <strong>[6622-92-0]2,6-dimethyl-4-hydroxypyrimidine</strong> and 3.1 g (22.4 mmol) of potassium carbonate were stirred in 35 ml of dimethylformamide for 30 minutes at 60 C. 4.04 g (15 mmol) of methyl alpha-(2-bromomethyl-phenyl)-beta-methylacrylate was then added. The reaction mixture was stirred for 4 hours at 75 C., and then for 15 hours at 20 to 25 C. It was then taken up in water and extracted with methyl tert-butyl ether. The organic phase was washed twice with sodium bicarbonate solution and twice with water, dried over sodium sulfate and evaporated down. The crude produce was purified chromatographically on silica gel with methyl tert-butyl ether/cyclohexane (8/1). There was obtained 3.2 g (68%) of the above compound in the form of pale yellow crystals (m.p.: 56-58 C.).
SYNTHESIS EXAMPLE 1 Synthesis of N-(2-methylbenzyl)-2-(2,4-dimethyl-6-pyrimidi-nyloxy)butylamide (Compound No. 96) To 50 ml of acetone were dissolved 2.6 g (0.021 mol) of <strong>[6622-92-0]2,4-dimethyl-6-hydroxypyrimidine</strong> and 5.2 g (0.091 mol) of N-(2-methylbenzyl)-2-bromobutylamide, and then 3.5 g (0.025 mol) of anhydrous potassium carbonate powder was added thereto, followed by heating under reflux with stirring. The reaction solution was poured into water, and the product formed was extracted with ethyl acetate. The ethyl acetate layer was washed successively with dilute caustic soda and water and then dried over glauber's salt. Subsequently, the solvent was distilled off and the resulting crude crystal was recrystallized from ethanol to give N-(2-methylbenzyl)-2-(2,4-dimethyl-6-pyrimidinyloxy)butylamide with m.p. 156 to 157 C. as a colorless needle crystal, at an yield of 58% relative to N-(2-methylbenzyl)-2-bromobutylamide.
<strong>[6622-92-0]2,4-dimethyl-6-hydroxy-pyrimidine</strong> [(518] mg, 4. 17 mmol) was dissolved in 7 mL anhydrous DMSO. Sodium tert-butoxide (382 mg, 3.98 mmol) was added in one portion and the mixture was stirred for 15 min at room temperature, until all the solids had dissolved. [4-FLUORO-NITRONAPHTHALENE] (725 mg, 3.79 mmol) was then added in one portion and the mixture was heated to [65 C] and stirred for 2 h. The color immediately had changed to green. The reaction was then allowed to cool back to room temperature, and was left standing overnight. It was then quenched with water and extracted with EtOAc (3X). The combined organic extracts were washed twice with water and once with brine, dried [(MGS04),] filtered and concentrated in vacuo, providing 1.2 g of the desired ether intermediate as an orange solid that was used as is without further purification
With dmap; In dichloromethane; at 20℃; for 0.0833333h;Microwave irradiation;
General procedure: The corresponding 4-pyrimidinol (1.07 mmol) and DMAP (1.61 mmol) were dissolved in CH2Cl2 (5.0 mL) in a 20-mL vessel, then TsCl (1.07 mmol) was added and the resulting mixture was irradiated for 5 min. The mixture was then diluted with sat. aq NaHCO3 (5.0 mL) and extracted with CH2Cl2 (3 × 15 mL). The combined organic phases were dried (anhyd Na2SO4) and filtered. The filtrate was rotary evaporated and the crude product was purified by column chromatography (silica gel, hexane/EtOAc mixtures).
With sodium ethanolate; In ethanol; for 20h;Reflux;
2,6-dimethylpyrimidin-4-ol. Ethyl 3-oxobutanoate (10.0 g, 77 mmol) and acetimidamide hydrochloride (7.23 g, 77 mmol) were added to the solution of sodium ethanolate (10.5 g, 154 mmol) in ethanol (200 mL). And the mixture was refluxed for 20 hours. Water (10 mL) was added to the mixture. The resultant mixture was concentrated to give a residue. The residue was purified by column chromatography (silica gel, dichloromethane /methanol = 15: 1) to give 2,6-dimethylpyrimidin-4-ol as a yellow solid (3.43 g, 36%). LRMS (M + H+) m/z: calcd 124.06; found 124.
29%
With potassium carbonate; In water; at 20℃; for 0.25h;Microwave irradiation;
General procedure: The corresponding amidine hydrochloride (2.54 mmol) and powdered K2CO3 (5.76 mmol) were dissolved in water (5.0 mL) in a 20-mL vessel. The beta-keto ester (2.31 mmol) was added and the resulting mixture was irradiated for 5-15 min (see Table 2). Upon the end of the reaction (TLC, hexanes/EtOAc, 5:1), the mixture was diluted with sat. aq NH4Cl (5.0 mL) and extracted with CH2Cl2 (3 × 15 mL). The combined organic phases were dried (anhyd Na2SO4) and filtered. The filtrate was rotary evaporated and the obtained crude product was purified by column chromatography [silica gel, hexane/EtOAc mixtures or recrystallized (EtOH)].
Example 326Synthesis of (1R,2S)-2-[(2,4-dimethyl-6-oxo-1,6-dihydropyrimidin-5-yl)oxy]methyl}-2-(3-fluorophenyl)-N-(5-fluoropyridin-2-yl)cyclopropanecarboxamide (326)(1) 2,6-dimethylpyrimidin-4-ol (326-1)Sodium (3.6 g) was added by portions to ethanol (92 ml) over 2 hours, while the solution was stirred at room temperature. Thereafter, ethyl acetoacetate (10 ml) and acetamidine hydrochloride (7.42 g) were added to the reaction solution, and the obtained mixture was stirred at 70 C. for 16 hours. Thereafter, the reaction mixture was stirred at 100 C. for 9 hours, and the temperature of the reaction solution was returned to room temperature. Concentrated hydrochloric acid was added to the reaction solution, so that the pH value was adjusted to around 5. The obtained mixture was concentrated under reduced pressure, so as to obtain a crude title compound (25.6 g).1H-NMR (400 MHz, CDCl3) delta (ppm): 2.30 (s, 31-1), 2.46 (s, 3H), 6.17 (s, 1H)
1,4-diaza-bicyclo[2.2.2]octane; In ethanol; at 80℃; for 18h;
Example 14:7-Amino-5-(3-bromo-4,5-dimethoxy-phenyl)-2,4-dimethyl-5H-pyrano[2,3-d]pyrimidine-6-(14)4-Hydroxy-2,6-dimethylpyrimidine (546 mg, 4.4 mmol), 3-bromo-4,5-dimethoxy-benzaldehyde (1077 mg, 4.4 mmol) and malononitrile (295 mg, 4.4 mmol) were taken in 2 ml ethanol at room temperature, charged with DABCO (48.4 mu, 1.46 mmol) and then stirred at 80 C under LC-MS control for 18 h. The reaction mixture was then cooled down to room temperature. The mixture was diluted with water to about 100 ml, stirred at room temperature for 1 h and the precipitates were separated by filtration. It was washed well with 50 % aqueous ethanol and dried under vacuum (1.52 g, 3.64 mmol, 82.8 %).
82.8%
With 1,4-diaza-bicyclo[2.2.2]octane; In ethanol; at 20 - 80℃; for 18h;
4-Hydroxy-2,6-dimethylpyrimidine (546 mg, 4.4 mmol), 3-bromo-4,5-dimethoxy-benzaldehyde (1077 mg, 4.4 mmol) and malononitrile (295 mg, 4.4 mmol) were taken in 2 ml ethanol at room temperature, charged with DABCO (48.4 mu, 1.46 mmol) and then stirred at 80 C under LC-MS control for 18 h. The reaction mixture was then cooled down to room temperature. The mixture was diluted with water to about 100 ml, stirred at room temperature for 1 h and the precipitates were separated by filtration. It was washed well with 50 % aqueous ethanol and dried under vacuum (1.52 g, 3.64 mmol, 82.8 %).
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