* 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.
Formic acid, 255.7g (ie, 38.3g of water) and 99percent of diisopropylamine, 460g, with a purity of 85percent, are added to a 1-liter autoclave,The stirrer was started to mix well and a homogeneous reaction system was obtained. The molar ratio of formic acid to diisopropylamine is 1.05:1.While maintaining the stirring, the above homogeneous reaction system is heated up to about 200° C., the pressure in the autoclave rises to about 1.7 MPa and no longer increases, the reaction is maintained for about 3 hours, and the autoclave is vented and discharged. The carbon monoxide and water vapor were collected and the reaction product was collected to obtain about 709 g of a uniform and transparent solution.
Reference：
[1] Research on Chemical Intermediates, 2013, vol. 39, # 6, p. 2843 - 2848
[2] Comptes Rendus Chimie, 2012, vol. 15, # 11-12, p. 980 - 987
[3] Bulletin of the Korean Chemical Society, 2010, vol. 31, # 10, p. 2989 - 2991
[4] Synlett, 2010, # 8, p. 1231 - 1234
[5] Synlett, 2010, # 14, p. 2093 - 2096
[6] Journal of Organic Chemistry, 2006, vol. 71, # 17, p. 6652 - 6654
[7] Green Chemistry, 2012, vol. 14, # 3, p. 847 - 854
[8] Journal of the American Chemical Society, 1955, vol. 77, p. 498,2456
[9] Monatshefte fuer Chemie, 1951, vol. 82, p. 330,335
[10] U.S.Dep.Agric.ARS, 33-17<1956>,
[11] Monatshefte fuer Chemie, 1962, vol. 93, p. 476 - 482
[12] Patent: CN107501115, 2017, A, . Location in patent: Paragraph 0076-0080
2
[ 124-38-9 ]
[ 108-18-9 ]
[ 2700-30-3 ]
Yield
Reaction Conditions
Operation in experiment
13 %Spectr.
Stage #1: With sodium hydride In N,N-dimethyl-formamide at 20℃; for 0.0833333 h; Sealed tube Stage #2: With diphenylsilane In N,N-dimethyl-formamide at 20℃; for 18 h; Sealed tube
General procedure: 0.05mmol equivalent of poly-imidazolium, an equimolar amount of sodium hydride, and 2mL of anhydrous DMF were placed in a crimp-top vial (8mL). The vial was sealed, and the suspension was stirred for 2h before CO2 was introduced via a balloon. Amines (1mmol) were subsequently added, and the reaction mixture was then allowed to stir for 5min before 2.5 equivalents of silane were added. The reaction was allowed to stir for 18h. After the reaction was completed, the reaction mixture was centrifuged, a 400-μL aliquot was sampled, and 20μL of mesitylene was added. An aliquot was then taken for NMR spectroscopy. For catalyst recycling, the remaining solution was decanted, and 2mL of fresh DMF was added. The reaction was allowed to stir for 30min before centrifuging and removal of DMF. This procedure was repeated at least three times using DMF (1×) and dichloromethane (3×) as the washing solvent. The recovered catalyst was then dried under the Schlenk line, and used directly for the next run.
Reference：
[1] Chemistry - An Asian Journal, 2018, vol. 13, # 20, p. 3018 - 3021
[2] Angewandte Chemie - International Edition, 2018, vol. 57, # 30, p. 9336 - 9340[3] Angew. Chem., 2018, vol. 130, p. 9480 - 9484,5
[4] Angewandte Chemie - International Edition, 2012, vol. 51, # 1, p. 187 - 190
[5] Journal of the American Chemical Society, 2012, vol. 134, # 6, p. 2934 - 2937
[6] Catalysis Science and Technology, 2014, vol. 4, # 6, p. 1529 - 1533
[7] Chemistry - A European Journal, 2016, vol. 22, # 46, p. 16489 - 16493
[8] Journal of Catalysis, 2016, vol. 343, p. 46 - 51
[9] Chemical Communications, 2017, vol. 53, # 57, p. 8046 - 8049
[10] Chemical Communications, 2017, vol. 53, # 68, p. 9502 - 9504
[11] ACS Catalysis, 2016, vol. 6, # 11, p. 7876 - 7881
4-chloro-2-diisopropylaminomethyleneamino-5-iodopyrimidine[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
In dichloromethane;
EXAMPLE 2 Preparation of 4-chloro-2-diisopropylaminomethyleneamino-5-iodopyrimidine A solution of 4.5 mL of oxalyl chloride in 35 mL of dichloromethane was added dropwise over 25 minutes to an ice water bath-cooled solution of 7.0 mL of N,N-diisopropylformamide in 65 mL of dichloromethane with magnetic stirring. After a few minutes, 4.74 g of 2-amino-4-hydroxy-5-iodopyrimidine was added in one portion. The bath was removed and the solution was stirred at room temperature for 30 minutes, then refluxed for one and one half hours. The solution was cooled and poured into an equal amount of ice-cold saturated aqueous sodium bicarbonate with stirring. The two phases were partitioned and the organic layer washed with additional bicarbonate(2*), water(1*) and finally saturated aqueous brine. After drying over sodium sulfate and filtration, the solution was evaporated in vacuo to yield 10.13 g of a reddish oil. The oil was purified by column chromatography on silica gel, eluding with dichloromethane. Like fractions were pooled, evaporated and triturated with hexanes to give white free flowing crystals, 5.94 g, m.p. 97-100 C.
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