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With oxalyl dichloride; N,N-dimethyl-formamide; In 1,2-dichloro-ethane; for 3h;Heating / reflux;
To a stirred solution containing 7.7 mL (99 MMOL) of DMF and 150 mL of DICHLOROETHANE at 0C was added 12.7 mL (144.6 MMOL) of OXALYL chloride slowly to control vigorous gas evolution. After the evolution of gas had ceased, 10.0 g of iodopyrimidone was added and the reaction mixture was heated at reflux for 3h, then cooled to room temperature and partitioned between water and DICHLOROMETHANE. The organic layers were dried over MGS04 and the solvent was removed under reduced pressure to give 9.6 g (88%) of the title COMPOUND. 1H-NMR (300 MHz, CDCI3) A 8. 89 (s, 1H) and 8.98 (s, 1H) ; ESIMS : 241.1 (M+H)+
83%
With oxalyl dichloride; In 1,2-dichloro-ethane; N,N-dimethyl-formamide; for 2h;Reflux;
Oxalyl chloride (1 .27 ml, 14.61 mmol) was added dropwise in 707 ml dimethylformamide and 20 ml dichloroethane. 5-lodopyrimidin-4(3/-/)-one ( 1 g, 4.55 mmol) was added and the reaction was heated at reflux for 2 h. The reaction mixture was dissolved in dichloromethane, washed with water, dried over sodium sulphate, filtered and concentrated under reduced pressure to give 0.91 g (83 % yield) of the title compound as a solid. Purity 100%.LRMS (m/z): 241 (M+1 )+
75.9%
With oxalyl dichloride; In 1,2-dichloro-ethane; N,N-dimethyl-formamide; at 0 - 85℃; for 4h;
N,N-dimethylformamide (3.9 mL, 27.0 mmol) was dissolved in 1,2-dichloroethane (90 mL) at 0 C, the reaction was stirred for 10 min, and oxalyl chloride (6.8 mL, 27.0 mmol) was added dropwise. ),After 20 minutes of dropwise addition, 5-iodopyrimidine-4(3H)one (5.0 g, 22.5 mmol) was added.The temperature was raised to 85 C for 4.0 h, and the reaction solution was concentrated.The residue was dissolved in dichloromethane (120 mL).The organic phase was washed with saturated brine (20 mL×2).Dry anhydrous sodium sulfate (20g),Filter and concentrate to give 4.1 g of a brown oil.The yield was 75.9%. The product was directly subjected to the next reaction without purification.
With trichlorophosphate; In methanol; water; toluene;
Method V Preparation of 4-Chloro-5-iodopyrimidine 5-Iodo-4(3H)-pyrimidinone (1 eq.) was suspended in toluene to which was added POCl3 (2.0 eq.). The reaction mixture was heated to reflux for 3 hours, and then cooled and concentrated. The residue was suspended in water, adjusted to pH=7 by addition of 4N sodium hydroxide, and extracted with ethyl acetate. The organic extracts were washed with brine, dried (MgSO4), filtered and stripped to give a red oil. The crude product was dissolved in methanol and silica gel was added. Following concentration, the coated silica gel was loaded onto a plug of silica gel and elution with ethyl acetate/hexanes yielded the title compound.
With trichlorophosphate; In toluene; for 3h;Heating / reflux;
Method 0 Preparation of 4-Chloro-5-iodopyrimidine 5-Iodo-4(3H)-pyrimidinone (1 eq. ) was suspended in toluene to which was added POC13 (2.0 eq. ). The reaction mixture was heated to reflux for 3 hours, and then cooled and concentrated. The residue was suspended in water, adjusted to pH=7 by addition of 4N sodium hydroxide, and extracted with ethyl acetate. The organic extracts were washed with brine, dried (MgS04), filtered and stripped to give a red oil. The crude product was dissolved in methanol and silica gel was added. Following concentration, the coated silica gel was loaded onto a plug of silica gel and elution with ethyl acetate/hexanes yielded the title compound.
Step 2. Preparation of 4-chloro-5-iodopirnidine; A mixture of 5-iodopyrimidin-4-ol (14.9 g, 67.1 mmol) in phosphorous oxychloride (25.0 ml, 268 mmol) with a water-cooled reflux condenser fitted with a drying tube was heated to reflux in a 135 C. bath for 3 h. The purple solution was cooled until warm and poured onto ice with swirling. The ice-cold mixture was basified with 6N NaOH, with addition of ice to maintain the cool temperature. The resulting brown precipitate was collected by filtration, rinsed with water, and dried in vacuo to give 4-chloro-5-iodopyrimidine as an orange solid. MS m/z=241 [M+H]+. Calc'd for C4H2IClN2: 240.4.
4 g
With oxalyl dichloride; In 1,2-dichloro-ethane; N,N-dimethyl-formamide; at 0 - 85℃; for 5h;
At 0 C,N,N-dimethylformamide (2.0 g, 27.0 mmol) was dissolved in 1,2-dichloroethane (60 mL), and stirred for 30 min.Oxalyl chloride (3.4 g, 27.0 mmol) was slowly added dropwise, and after the addition was completed,The solution is viscous,Add compound 4-hydroxy-5-iodopyrimidine(5g, 22.5mmol),The temperature was slowly raised to 85 C and the reaction was stirred for 5.0 h. concentrate,The residue was dissolved in dichloromethane (70 mL).The organic phase was washed once with distilled water (30 mL).Dry anhydrous sodium sulfate (12g), concentrated,4.0 g of a reddish brown oil was obtained, which was directly subjected to the next reaction.
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