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With ammonium hydroxide; sodium hydrogencarbonate; In tetrahydrofuran; at 55℃;
To a solution of the compound 4,6-dichloro-5-nitropyrimidine (9.7 g, 50 mmol) in tetrahydrofuran (100 mL) was added aqueous ammonia (100 mL) and sodium bicarbonate (4.6 g, 55 mmol), heated to 55 C and stirred overnight. The reaction was cooled to room temperature and the organic solvent was removed under reduced pressure. The residue was filtered and separated by flash column chromatography (dichloromethane: methanol = 100: 1) to give the title compound A: 6-chloro-5-nitropyrimidine- 4-amine (8.1 g, yield 93%).
With ammonium hydroxide; In methanol; diethyl ether; water; for 2.0h;Industry scale;
6-Chloro-5-nitropyrimidin-4-amine[00161] A solution of 28% aqueous ammonium hydroxide (670 mL, 5.35 mol, 1.04 equiv) was added in a drop-wise fashion to a rapidly stirred solution of the 4,6-dichloro-5- nitropyrimidine solid (1000 g, 5.16 mol, 1.00 equiv) in diethyl ether (4000 mL) and methanol (670 mL). The addition was carried out over a period of 2 hours. Upon completion of addition, the resulting yellow solid was filtered off, washed with water and hexane, and dried under reduced pressure to give the title compound as a yellow solid (yield: 675 g). This crude solid was used in the next step without any further purification. NMR (400 MHz, DMSO- d6): delta 8.97 (s, 1H), 7.91 (broad s, 2H). MS (EI) for C4H3CIN4O2: 175 (MH+).
Sodium methoxide (2.70 g, 50.0 mmol) was added portionwise over 10 min to a 0C suspension OF 4, 6-DICHLORO-5-NITROPYRIMIDINE (4.85 g, 25.0 mmol) in methanol (90 ml). On complete addition the mixture was stirred at 0C for 2 h. The precipitate was filtered and the filtrate evaporated. The residue was suspended in isohexane and filtered. The filtrate was evaporated and the residue purified by flash column chromatography on silica, eluting with 5% ethyl acetate in isohexane. Collecting appropriate fractions gave 4-chloro-6-methoxy-5- nitropyrimidine (3.50 g, 74%) as a white solid
40%
In methanol; at 0℃; for 4.0h;
a) 4-Chloro-6-methoxy-5-nitropyrimidine Sodium methoxide (2.94 g, 54.4 mmol) was added portionwise to a cooled (ice-bath) stirred suspension of 4,6-dichloro-5-nitropyrimidine (5.00 g, 25.8 mmol) in anhydrous methanol (90 mL). After 4 hours stirring at 0 C the mixture was filtered and the filtrate was concentrated in vacuo. The mixture was suspended in hexane, refiltered and the filtrate was concentrate to give an oil which was purified by by flash chromatography (5:1 hexanes/ethyl acetate) to give the title compound (1.97 g, 40%) as a yellow solid. LRMS (m/z): 190 (M+1)+. 1H NMR delta (300 MHz, CDCl3): 4.19 (s, 3H), 8.57 (s, 1H).
40%
In methanol; at 0℃; for 4.0h;Cooling with ice;
a) 4-Chloro-6-methoxy-5-nitropyrimidineSodium methoxide (2.94 g, 54.4 mmol) was added portion wise to a cooled (ice-bath) stirred suspension of 4,6-dichloro-5-nitropyrimidine (5.00 g, 25.8 mmol) in anhydrous methanol (90 mL). After 4 hours stirring at 0 C the mixture was filtered and the filtrate was concentrated in vacuo. The mixture was suspended in hexane, refiltered and the filtrate was concentrate to give an oil which was purified by flash chromatography (5:1 hexanes/ethyl acetate) to give the title compound (1 .97 g, 40%) as a yellow solid.LRMS (m/z): 190 (M+1 )+.1H NMR delta (300 MHz, CDCI3): 4.19 (s, 3H), 8.57 (s, 1 H).
[[00313]] 4, 6-Dichloro-5-aminopyrimidine (5.8 g, 0.036 mol) was diluted in [ETOH] (25 ml) and toluene (100 ml). A 2M [NA2CO3] (45.0 ml) was added followed by Pd (PPh3) 2Cl2 (1.5 g, 0.0021 mol), and <strong>[219735-99-6]2-chloro-4-methoxyphenylboronic acid</strong> (0.035 mol). The reaction was warmed to reflux under an inert atmosphere for 5 hours. The reaction was then allowed to cool to room temperature and poured over [ETOAC/H2O.] The organic layer was separated and washed with sat'd sodium chloride, dried [(MGS04),] filtered and concentrated. The material was flushed through a plug of silica using [50%] EtOAc/hexane as an eluting solvent. The crude material was concentrated in vacuo and diluted in 5 ml butanol. [4-HEPTYAMINE] was added to the solution and the mixture warmed to reflux for 18 hours. After concentrating the solution in vacuo and purification on silica gel using 80% EtOAc/hexane as the eluting solvent the desired intermediate [6- (2-CHLORO-4-METHOXY-PHENYL)-N4- (1-PROPYL-BUTYL)-] pyrimidine-4, 5-diamine was isolated (0.29 g, 73%). MS (AP) 349.3 [[(M+H) +,] 100].
A suspension of 4,6-dichloro-5-nitropyrimidine (2.0 g, 10.2 mmol) in anh. MeOH (37 mL) was cooled to 0C and NaOMe (579 mg, 10.2 mmol) was portionwise added over 10 min. The rxn mixture was stirred for 30 min and filtered. The filtrate was concentrated in vacuo and the crude was purified by CC using Hept/EtOAc. LC-MS: tR=0.75 min 1H NMR (400 MHz, DMSO-d6) <5: 8.93 (s, 1 H), 4.14 (s, 3 H)
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