* 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] Chemische Berichte, 1919, vol. 52, p. 876
2
[ 1395342-97-8 ]
[ 6343-68-6 ]
Yield
Reaction Conditions
Operation in experiment
1.58 g
With hydrogenchloride In ethanol; water at 50℃; for 2 h;
General procedure: Prior to the reaction, the starting 5-substituted 2-amino-4,6-dihydroxypyrimidine A2–A11 was dried in a vacuum drier at 80 °C and under 0.1 mbar for 1 day, because crystalline water increases the amount of the Vilsmeier–Haack–Arnold reagent required for full conversion. Subsequently, 5-substituted 2-amino-4,6-dihydroxypyrimidine (10 mmol) was suspended under inert atmosphere in a 2 M solution of the Vilsmeier–Haack–Arnold reagent (80 mmol, 40 mL) in chloroform. The reaction mixture was subsequently heated at reflux for 4 h, during which the starting material was completely dissolved. The reaction mixture was cooled to the room temperature, poured onto ice and rapidly neutralized with a saturated aqueous NaHCO3 solution. The obtained mixture was quickly transferred into a separatory funnel and immediately extracted with chloroform(3 x 20 mL). The organic fractions were combined together,dried over MgSO4, filtered through a 0.5 cm layer of silica gel and concentrated down on a rotary evaporator. This crude residue of 5-substituted 4,6-dichloro-2-[(dimethylamino)methylene]amino}pyrimidine was dissolved in the mixture of 99 percent ethanol (20 mL) and 37 percentaqueous HCl (2 mL). The reaction mixture was heated at 50 °C for 2 h, during which a crystalline product began to precipitate directly from the reaction mixture. After that, water (30 mL) was added and the reaction mixture was intensively stirred for 10 min. The precipitated product was filtered off and washed with a water/ethanol mixture (1/1,2 x 10 mL), 5 percent aqueous solution of NaHCO3 (10 mL) and a water/ethanol mixture (1/1, 10 mL). The product was subsequently recrystallized from aqueous ethanol, filtered off, washed with a water/ethanol mixture (1/1, 10 mL) and dried under high vacuum.
With hydrogenchloride; In ethanol; water; at 50℃; for 2.0h;
General procedure: Prior to the reaction, the starting 5-substituted 2-amino-4,6-dihydroxypyrimidine A2-A11 was dried in a vacuum drier at 80 C and under 0.1 mbar for 1 day, because crystalline water increases the amount of the Vilsmeier-Haack-Arnold reagent required for full conversion. Subsequently, 5-substituted 2-amino-4,6-dihydroxypyrimidine (10 mmol) was suspended under inert atmosphere in a 2 M solution of the Vilsmeier-Haack-Arnold reagent (80 mmol, 40 mL) in chloroform. The reaction mixture was subsequently heated at reflux for 4 h, during which the starting material was completely dissolved. The reaction mixture was cooled to the room temperature, poured onto ice and rapidly neutralized with a saturated aqueous NaHCO3 solution. The obtained mixture was quickly transferred into a separatory funnel and immediately extracted with chloroform(3 x 20 mL). The organic fractions were combined together,dried over MgSO4, filtered through a 0.5 cm layer of silica gel and concentrated down on a rotary evaporator. This crude residue of 5-substituted 4,6-dichloro-2-[(dimethylamino)methylene]amino}pyrimidine was dissolved in the mixture of 99 % ethanol (20 mL) and 37 %aqueous HCl (2 mL). The reaction mixture was heated at 50 C for 2 h, during which a crystalline product began to precipitate directly from the reaction mixture. After that, water (30 mL) was added and the reaction mixture was intensively stirred for 10 min. The precipitated product was filtered off and washed with a water/ethanol mixture (1/1,2 x 10 mL), 5 % aqueous solution of NaHCO3 (10 mL) and a water/ethanol mixture (1/1, 10 mL). The product was subsequently recrystallized from aqueous ethanol, filtered off, washed with a water/ethanol mixture (1/1, 10 mL) and dried under high vacuum.
With hydrogenchloride; water; In ethanol; at 50℃; for 2.0h;
General procedure: Prior to the reaction, the starting 5-substituted 2-amino-4,6-dihydroxypyrimidine A2-A11 was dried in a vacuum drier at 80 C and under 0.1 mbar for 1 day, because crystalline water increases the amount of the Vilsmeier-Haack-Arnold reagent required for full conversion. Subsequently, 5-substituted 2-amino-4,6-dihydroxypyrimidine (10 mmol) was suspended under inert atmosphere in a 2 M solution of the Vilsmeier-Haack-Arnold reagent (80 mmol, 40 mL) in chloroform. The reaction mixture was subsequently heated at reflux for 4 h, during which the starting material was completely dissolved. The reaction mixture was cooled to the room temperature, poured onto ice and rapidly neutralized with a saturated aqueous NaHCO3 solution. The obtained mixture was quickly transferred into a separatory funnel and immediately extracted with chloroform (3 9 20 mL). The organic fractions were combined together, dried over MgSO4, filtered through a 0.5 cm layer of silica gel and concentrated down on a rotary evaporator. This crude residue of 5-substituted 4,6-dichloro-2-[(dimethylamino)methylene]amino}pyrimidine was dissolved in the mixture of 99 % ethanol (20 mL) and 37 % aqueous HCl (2 mL). The reaction mixture was heated at 50 C for 2 h, during which a crystalline product began to precipitate directly from the reaction mixture. After that, water (30 mL) was added and the reaction mixture was intensively stirred for 10 min. The precipitated product was filtered off and washed with a water/ethanol mixture (1/1,2 9 10 mL), 5 % aqueous solution of NaHCO3 (10 mL) and a water/ethanol mixture (1/1, 10 mL). The product was subsequently recrystallized from aqueous ethanol, filtered off, washed with a water/ethanol mixture (1/1, 10 mL) and dried under high vacuum.
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