* 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] Helvetica Chimica Acta, 1958, vol. 41, p. 1806,1812
2
[ 13162-43-1 ]
[ 39906-04-2 ]
Yield
Reaction Conditions
Operation in experiment
84%
With palladium 10% on activated carbon; hydrogen In ethyl acetate at 20℃; for 4 h;
General procedure: 10percent Pd/C(0.05) gwas added to the solution of substituted pyrimidine (4.48mmol) in ethyl acetate (EA, 20mL) in Parr hydrogenater. Then, replace the air with nitrogen three times, and react for 4hat room temperature in normal pressure. Filter the solution to remove Pd/C through Celite filter agent, the filtrate was concentrated to yield the intermediates 11a,b [46]. 5.4.1 4,6-Dichloro-2-methyl-5-nitropyrimidine (11a) Pale solid; Yield: 84.0percent; MS (ESI) m/z: 177.94 [M+H]+.
Reference：
[1] European Journal of Medicinal Chemistry, 2017, vol. 140, p. 212 - 228
[2] Chemistry of Heterocyclic Compounds (New York, NY, United States), 1983, p. 1113 - 1115[3] Khimiya Geterotsiklicheskikh Soedinenii, 1983, vol. 19, # 10, p. 1398 - 1400
[4] Journal of the Chemical Society, 1954, p. 3832,3833
[5] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 17, p. 5721 - 5726
[6] RSC Advances, 2016, vol. 6, # 82, p. 78762 - 78767
Reference：
[1] Chemistry of Heterocyclic Compounds (New York, NY, United States), 1983, p. 1113 - 1115[2] Khimiya Geterotsiklicheskikh Soedinenii, 1983, vol. 19, # 10, p. 1398 - 1400
[3] Helvetica Chimica Acta, 1958, vol. 41, p. 1806,1812
5
[ 53925-27-2 ]
[ 13162-43-1 ]
Yield
Reaction Conditions
Operation in experiment
77%
at 100 - 120℃; for 2 h;
[00859] This nitropyrimidine (205 mg, 1.2 mmol) was dissolved in phosphoryl chloride (1 ml) and diethylaniline (0.3 ml, 1.9 mmol) was added thereto, and the mixture was stirred for 1 hour at 100° C. and for 1 hour at 120° C. The reaction solution was added to ice and then extracted with ethyl acetate. The organic layer was washed with water and then with a saturated aqueous solution of sodium chloride, and dried over magnesium sulfate. Thereafter, the solvent was distilled off, and the resulting crude product was purified through silica gel chromatography (eluent-hexane:ethyl acetate=20:1) to obtain 194 mg (yield 77percent) of 4,6-dichloro-2-methyl-5-nitropyrimidine as a colorless needle crystal.
Reference：
[1] Asian Journal of Chemistry, 2014, vol. 26, # 12, p. 3559 - 3561
[2] Patent: US6849647, 2005, B1, . Location in patent: Page/Page column 134
[3] Journal of Medicinal Chemistry, 2000, vol. 43, # 22, p. 4288 - 4312
[4] Patent: US6107300, 2000, A,
[5] Patent: US6245769, 2001, B1,
[6] Patent: US6348466, 2002, B1, . Location in patent: Page column 14
[7] Patent: EP2143724, 2010, A1, . Location in patent: Page/Page column 42
[8] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 17, p. 5721 - 5726
6
[ 53925-27-2 ]
[ 13162-43-1 ]
Yield
Reaction Conditions
Operation in experiment
49%
With trichlorophosphate In n-heptane; toluene
(b) 2-Methyl-4,6-dichloro-5-nitropyrimidine. To a round-bottomed flask equipped with a Dean-Stark trap, reflux condenser, pressure-equalized addition funnel, magnetic stirrer, heating mantel and internal temperature probe was added 2-methyl-4,6-dihydroxy-5-nitropyrimidine (Example 76(a)) (2.0 g, 11 mmol) and toluene (16 mL). The Dean-Stark trap was filled with toluene (12 mL). For 3 h, the reaction mixture was heated at reflux during which time water collected in the Dean-Stark trap. Heat was removed from the reaction vessel, and after 20 min, diisopropylethylamine (Aldrich Chemical Company) (2.8 mL, 16 mmol) was poured into the reaction mixture through the reflux condenser. The reaction mixture was heated at ref lux again, and POCl3 (Aldrich Chemical Company) (7 mL, 74 mmol) was added through the addition funnel at such a rate as to maintain the internal temperature below 113° C. (8 min). Vigorous bubbling was observed during the addition of POCl3. Following this addition, the reaction mixture was heated for an additional 3 h at reflux. Heat was then removed from the flask, and the reaction was stirred at room temperature for 18 h. The reaction mixture was then poured onto ice-water (100 mL), shaken in a separatory funnel, and filtered through a pad of Celite. The organic layer was collected from the filtrate, and the aqueous layer was extracted twice with ether. All organic fractions were combined, dried over Na2SO4, and concentrated in vacuo. Heptane was added to the residue, the contents were filtered through a pad of Celite, and concentrated in vacuo to give the title compound (1.1 g, 49percent) as a brown rod-like crystals in sufficient purity for the next step. 1H NMR (DMSO-d6; 400 MHz): δ 2.5 (s,3). 13C NMR (DMSO-d6; 100.6 MHz): δ 27.04, 127.0, 153.6, 170.8.
Reference：
[1] Patent: US6187777, 2001, B1,
7
[ 1194-22-5 ]
[ 13162-43-1 ]
Reference：
[1] Journal of Medicinal Chemistry, 2000, vol. 43, # 22, p. 4288 - 4312
Reference：
[1] Chemische Berichte, 1938, vol. 71, p. 87,99
[2] Journal of the Chemical Society, 1944, p. 678
[3] Journal of the Chemical Society, 1954, p. 3832,3833
10
[ 40497-30-1 ]
[ 13162-43-1 ]
Reference：
[1] Journal of the Chemical Society, 1954, p. 3832,3833
[2] Chemische Berichte, 1938, vol. 71, p. 87,99
11
[ 53925-27-2 ]
[ 10025-87-3 ]
[ 13162-43-1 ]
Reference：
[1] Patent: US6342503, 2002, B1, . Location in patent: Example 101
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