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c) Pyrimidine-4-carbaldehyde A solution of 4-dimethoxymethyl-pyrimidine (30.6 g, 199 mmol) in water (235 mL) and concentrated sulfuric acid (2.9 g, 30 mmol) was heated at 60° C. for 24 h. After cooling to room temperature the pH was set to 8 with saturated aqueous sodium hydrogen carbonate solution. The mixture was then extracted overnight in a continuous extraction (Keberle) for 48 h with chloroform. The chloroform extract was then dried over sodium sulfate, filtered and evaporated. Purification by chromatography (SiO2, dichloromethane:methanol=1:0 to 95:5) afforded the title compound (8.1 g, 26percent) which was obtained as a brown oil. MS: m/e=108.0 [M]+.
26%
With hydrogenchloride In water at 60 - 70℃; for 24 h;
Pyrimidine-4-carbaldehyde (C12) A solution of 4-(dimethoxymethyl)pyrimidine (C11) (90 g, 0.58 mol) and concentrated hydrochloric acid (10 mL) in water (300 mL) was heated at 60-70° C. for 24 hours. The mixture was cooled and evaporated under reduced pressure to afford a glass-like mass, which was basified with aqueous potassium carbonate solution and extracted with ethyl acetate. The combined organic layers were concentrated in vacuo, and the residue was purified by distillation to afford the product as an oil. Yield: 16.3 g, 0.15 mol, 26percent. GCMS m/z 108.0 (M+). 1H NMR (400 MHz, DMSO-d6) δ 7.90 (dd, J=5.0, 1.5 Hz, 1H), 9.14 (d, J=5.0 Hz, 1H), 9.49 (d, J=1.5 Hz, 1H), 9.96 (s, 1H).
4-(Dimethoxymethyl)pyrimidine (C11) A mixture of (3E)-4-(dimethylamino)-1,1-dimethoxybut-3-en-2-one (C10) (147 g, 0.85 mol) and formamidine acetate (131 g, 1.26 mol) was heated at 110-120° C. for 4 hours. After cooling to room temperature, the reaction was poured into water (250 mL) and extracted with chloroform (5*100 mL). The combined organic layers were dried over sodium sulfate, filtered, and concentrated in vacuo. Distillation of the residue under vacuum afforded the product as an oil. Yield: 84 g, 0.54 mol, 64percent. Boiling point: 45-50° C./0.2 torr. NMR data was obtained using the product of a reaction run under similar conditions. 1H NMR (400 MHz, CDCl3) δ 3.30 (s, 6H), 5.21 (s, 1H), 7.46 (dd, J=5.1, 1.4 Hz, 1H), 8.68 (d, J=5.1 Hz, 1H), 9.12 (d, J=1.4 Hz, 1H).
b) 4-Dimethoxymethyl-pyrimidine A mixture of (E)-4-dimethylamino-1,1-dimethoxy-but-3-en-2-one (49.6 g, 286 mmol) and formamidine acetate (44.7 g, 429 mmol) was heated at 120 C. for 4 h. After cooling to room temperature the mixture was poured into water and extracted with dichloromethane. The combined organic extracts were then dried over sodium sulfate, filtered and evaporated. Purification by distillation afforded the title product (31 g, 70%) as a colourless liquid. Bp 59-60 C. at 1.3 mbar. MS: m/e=155.0 [M+H]+.
64%
at 110 - 120℃; for 4h;
4-(Dimethoxymethyl)pyrimidine (C11) A mixture of <strong>[67751-23-9](3E)-4-(dimethylamino)-1,1-dimethoxybut-3-en-2-one</strong> (C10) (147 g, 0.85 mol) and formamidine acetate (131 g, 1.26 mol) was heated at 110-120 C. for 4 hours. After cooling to room temperature, the reaction was poured into water (250 mL) and extracted with chloroform (5*100 mL). The combined organic layers were dried over sodium sulfate, filtered, and concentrated in vacuo. Distillation of the residue under vacuum afforded the product as an oil. Yield: 84 g, 0.54 mol, 64%. Boiling point: 45-50 C./0.2 torr. NMR data was obtained using the product of a reaction run under similar conditions. 1H NMR (400 MHz, CDCl3) delta 3.30 (s, 6H), 5.21 (s, 1H), 7.46 (dd, J=5.1, 1.4 Hz, 1H), 8.68 (d, J=5.1 Hz, 1H), 9.12 (d, J=1.4 Hz, 1H).
c) Pyrimidine-4-carbaldehyde A solution of 4-dimethoxymethyl-pyrimidine (30.6 g, 199 mmol) in water (235 mL) and concentrated sulfuric acid (2.9 g, 30 mmol) was heated at 60 C. for 24 h. After cooling to room temperature the pH was set to 8 with saturated aqueous sodium hydrogen carbonate solution. The mixture was then extracted overnight in a continuous extraction (Keberle) for 48 h with chloroform. The chloroform extract was then dried over sodium sulfate, filtered and evaporated. Purification by chromatography (SiO2, dichloromethane:methanol=1:0 to 95:5) afforded the title compound (8.1 g, 26%) which was obtained as a brown oil. MS: m/e=108.0 [M]+.
26%
With hydrogenchloride; In water; at 60 - 70℃; for 24h;
Pyrimidine-4-carbaldehyde (C12) A solution of 4-(dimethoxymethyl)pyrimidine (C11) (90 g, 0.58 mol) and concentrated hydrochloric acid (10 mL) in water (300 mL) was heated at 60-70 C. for 24 hours. The mixture was cooled and evaporated under reduced pressure to afford a glass-like mass, which was basified with aqueous potassium carbonate solution and extracted with ethyl acetate. The combined organic layers were concentrated in vacuo, and the residue was purified by distillation to afford the product as an oil. Yield: 16.3 g, 0.15 mol, 26%. GCMS m/z 108.0 (M+). 1H NMR (400 MHz, DMSO-d6) delta 7.90 (dd, J=5.0, 1.5 Hz, 1H), 9.14 (d, J=5.0 Hz, 1H), 9.49 (d, J=1.5 Hz, 1H), 9.96 (s, 1H).
With bromine; sodium acetate; acetic acid; at 40℃; for 7.0h;
To the solution of 3.90 g of <strong>[25746-87-6]4-(dimethoxymethyl)pyrimidine</strong> (25.3 mmol) in 100 mLAcOll 4.15 g sodium acetate (50.6 mmol) and 8.08 g bromine (50.6 mmol) were addedand the mixture was stirred at 40C for 7 h. Reaction mixture was concentrated underreduced pressure, DCM was added to the residue, and it was washed with saturated aq.NaHCO3. The organic phase was dried over Na2SO4 and concentrated under reduced pressure. The crude product was purified via flash chromatography using heptane and EtOAc as eluents to give 5-bromo-<strong>[25746-87-6]4-(dimethoxymethyl)pyrimidine</strong>, 1HNMR(400 MHz, DMSO-d6): 9.18 (s, 111), 9.06 (s, 111), 5.51 (s, IH), 3.40 (s, 611).
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