Pyrimidines

56-09-7, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 56-09-7, name is 2-Amino-6-hydroxypyrimidin-4(3H)-one, molecular formula is C4H5N3O2, The compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

Stir POCl3 (84 ml, 0.9 mol) and chill to 5-10 C. while adding DMF (17.8 ml, 0.23 mol ) drop-wise. Allow the mixture to warm to room temperature (RT) and add 2-amino-4,6-dihydroxypyrimidine VI (14 g, 0.11 mol) portion-wise. Heat at 100 C. for 5 h. Strip off excess POCl3 under vacuum, pour the residue into ice water, and stir overnight. Collect solids by filtration and recrystallize the dried material from a filtered ethyl acetate (EtOAc) solution to give the aldehyde, VII, m.p. 230 (dec). Mass spectrum: M+=192. PMR (DMSO): delta 8.6(delta, 2H); delta 10.1(s,1H).

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles. 56-09-7, 2-Amino-6-hydroxypyrimidin-4(3H)-one, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Schering Corporation; US2005/239795; (2005); A1;,
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1193-24-4, Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 1193-24-4, name is 4,6-Dihydroxypyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

In a four-necked flask equipped with a reflux condenser, the temperature was raised and stirred, and 228 g of 4,6-dihydroxypyrimidine was added by a constant pressure dropping funnel, the content was 98%,and the content of 633 g of phosphorus oxychloride was 97%.The temperature was raised to 40 to 45 C, and the content of 408 g of triethylamine was added dropwise with content of 99%, after the addition was completed, the temperature was raised to 100 to 105 C and kept for 2 hours. HPLC (high performance liquid phase) analysis of 4,6-dihydroxypyrimidine was less than 0.2%, and the reaction was completed. 880g of toluene was added and cooled tom 0~5 C, 800g of ice water mixture was added, the ice was decomposed to room temperature, the organic phase was decomposed and the aqueous layer was extracted (200 ml of toluene), the organic phase was combined and washed with alkaline water until neutral. Toluene was concentrated. 697 g of toluene dichloropyrimidine solution was obtained, and the purity of 4, 6-dichloropyrimidine was 97.3%, and the content was 39.91%. The crude yield was 92%. The 697 g crude solution was divided into three 240 g, 240 g, 217 g, respectively, as 1, 2, 3, to do the distillation experiment: The temperature of the top of the steam packed tower is required to reach 94 C ~ 96 C, when the temperature was reached, the concentrated organic phase was added dropwise, the feed rate was controlled, the balance was adjusted to prevent the stripper tower from cooling; The obtained organic phase, the quality of the aqueous phase and the purity and concentration of 4,6-dichloropyrimidine are shown in Table 1, the obtained organic phase was concentrated, cooled, crystallized, centrifuged or filtered to obtain a high purity product. The refined yield was as high as 98% or more, and the appearance was white crystal. The experimental results are shown in Table 1.

While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant.we look forward to future research findings about 1193-24-4, 4,6-Dihydroxypyrimidine.

Reference:
Patent; Yueyang Zhenghao Chemical Technology Co., Ltd.; Huang Zhengliang; Li Guang; Yang Xiaoping; Wan Xing; Li Weiping; Li Xiping; Zhang Songbo; Fang Xiaolan; (7 pag.)CN108395409; (2018); A;,
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1193-24-4, Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 1193-24-4, name is 4,6-Dihydroxypyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

EXAMPLE 6 To a stirred mixture of 4,6-dihydroxypyrimidine (5.18 g, 1 equivalent) and N,N-diisopropylethylamine (11.75 g, 2 equivalents) in acetonitrile (100 ml) was added phosgene (28 g, 19.7 ml, 6.2 equivalents) in two aliquots. The resulting mixture was stirred for 10 minutes at room temperature and was then stirred for 4 hours at 55 C. The reaction mixture was sparged with air overnight after which water (100 ml) was added. The resulting mixture was extracted with dichloromethane (3*100 ml). The organic extracts were combined, washed with water (100 ml), dried over magnesium sulphate and evaporated to dryness to leave 4,6-dichloropyrimidine (6.35 g).

While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant.we look forward to future research findings about 1193-24-4, 4,6-Dihydroxypyrimidine.

Reference:
Patent; Zeneca Limited; US5750694; (1998); A;,
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171887-03-9, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 171887-03-9, name is N-(2-Amino-4,6-dichloropyrimidine-5-yl)formamide, molecular formula is C5H4Cl2N4O, The compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

Example 1: Preparation ofN-[2-amino-4-chloro-6-(3-methyl-4-nitro- benzylamino)-pyrimidin-5-yl]-formamideIsopropanol (1500 mL), N-(2-amino-4,6-dichloro-pyrimidin-5-yl)-fo?namide (100.0 g) and (3-methyl-4-nitrophenyl)methanamine hydrochloride (263.47 g) were charged to a 5L reactor. The temperature was increased to 58-65 0C, and triethylamine (341.85 mL) was added with vigorous stirring over a period of 30-40 min. The reaction mixture was heated to reflux for 3-4 hr. Reaction mass temperature was brought down to 15-20 0C, water (2000 mL) was added over a period of 30 min. Stirring was continued at 15-20 0C for another 1-2 hr. The reaction mass was filtered and washed with an isopropyl alcohol/water mixture (140 mL/180 mL) followed by water (215.0 mL) and cold isopropyl alcohol (95.0 mL). The product was dried at 40-45 0C for 10-15 hr under vacuum to yield 150-155 g (92-95%) of N-[2-amino-4-chloro-6-(3-methyl-4-nitro- benzylamino)-pyrimidin-5-yl]-formamide.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles. 171887-03-9, N-(2-Amino-4,6-dichloropyrimidine-5-yl)formamide, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BIOGEN IDEC MA INC.; VERNALIS RESEARCH LIMITED; WO2008/86201; (2008); A1;,
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1004-17-7, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 1004-17-7, name is 2-Methylpyrimidine-4-carbaldehyde, the common compound, a new synthetic route is introduced below.

99. (+)-2- 3,4-trans)-4-methyl-l-q2-methylpyrimidin-4- yl)methyl)pyrrolidin-3-yl)-7-ftetrahvdro-2H-pyran-4-yl)imidazo[5,l- f] ri,2,41triazin-4(3H)-one [1058] To a stirred solution of (-)-2-((3,4-trans)-4-methylpyrrolidin-3-yl)-7- (tetrahydro-2H-pyran-4-yl)imidazo[5,l- J[l,2,4]triazin-4(3H)-one (150 mg, 0.49 mmol) in MeOH (10 mL) was added 2-methylpyrimidine-4-carbaldehyde (66 mg, 0.54 mmol) at RT under argon atmosphere. After being stirred for 2 h, NaCNBH3 (92 mg, 1.47 mmol) was added to the reaction mixture and stirring was continued for another 16 h at RT. The volatiles were evaporated under reduced pressure. The residue was diluted with ice-cold water (15 mL) and extracted with DCM (2 x 20 mL). Combined organic layer was dried over sodium sulphate, filtered and concentrated in vacuo to obtain the crude product. The crude material was purified by silica gel column chromatography and then further purified by preparative HPLC to afford (+)-2-((3 ,4-trans)-4-methyl- 1 -((2-methylpyrimidin-4-yl)methyl)pyrrolidin-3 – yl)-7-(tetrahydro-2H-pyran-4-yl)imidazo[5,l- J[l,2,4]triazin-4(3H)-one (50 mg, 25%) as an off-white solid; 1H-NMR (DMSO d6, 400 MHz): delta 11.72 (bs, 1H), 8.64 (d, 1H), 7.67 (s, 1H), 7.32 (d, 1H), 3.97-3.93 (m, 2H), 3.84-3.68 (m, 2H), 3.52-3.47 (m, 2H), 3.41-3.37 (m, 1H), 3.06-2.38 (m, 4H), 2.69-2.65 (m, 2H), 2.58 (s, 3H), 2.37-2.32 (m, 4H), 1.09 (d, 3H); Mass (ESI): 410 [M++l]; LC-MS: 98.26%; 410.3 [M++l]; (column; X-bridge C-18, (50×3.0 mm, 3.5mu); RT 2.31 min. 5mM NH4OAc: ACN; 0.8 ml/min); HPLC (purity): 99.24%; (column; Eclipse XDB C-18, (150×4.6 mm, 5.0mu); RT 7.50 min. 5mM NH4OAc (Aq): ACN; 1.0 ml/min; Chiral HPLC: 100%, R, = 10.36 min (Chiralpak IA, 250 x 4.6mm, 5mu; mobile phase (A) 0.1% TEA in n- Hexane (B) IPA (A: B : 75:25); flow Rate: 1.00 mL/min); Optical rotation [a]D2: +69.96 (c = 0.25, DCM); TLC: 10% MeOH/DCM (Rf: 0.4).

Statistics shows that 1004-17-7 is playing an increasingly important role. we look forward to future research findings about 2-Methylpyrimidine-4-carbaldehyde.

Reference:
Patent; ENVIVO PHARMACEUTICALS, INC.; RIPKA, Amy; SHAPIRO, Gideon; MCRINER, Andrew, J.; BURSAVICH, Matthew, Gregory; WO2013/142269; (2013); A1;,
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1780-26-3, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 1780-26-3, name is 2-Methyl-4,6-dichloropyrimidine, molecular formula is C5H4Cl2N2, The compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

To a cooled solution of 2-amino-N-(2-chloro-6-methylphenyl)-1,3-thiazole-5- carboxamide( 100 gm) and 4,6-Dichloro-2-methylpyrimidine(66. 96 gm) in THF(5 00 ml), was added sodium tert-butoxide(125.62 gm). The reaction mixture was allowed to cooled at 0-10C. Concentrated HC1 (80 ml) was added. The reaction mixture was heated to 25¡À5C for 1-2h and was cooled to 0-10C. The precipitated solid was filtered, washed with water (200 ml) and dried to obtain N-(2-Chloro-6-methylphenyl)-2-[(6-chloro-2- methylpyrimidin-4-yl) amino] -1, 3 -thiazole-5 -carboxamide (90gm).

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles. 1780-26-3, 2-Methyl-4,6-dichloropyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ALEMBIC PHARMACEUTICALS LIMITED; JAYARAMAN, Venkatraman; PATEL, Samir; MISTRY, Samir; PARMAR, Bhupendra; WO2015/49645; (2015); A2;,
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705-24-8 , The common heterocyclic compound, 705-24-8, name is 4,6-Dichloro-2-(trifluoromethyl)pyrimidine, molecular formula is C5HCl2F3N2, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route.

To a solution of 4,6-dichloro-2-(trifluoromethyl)pyrimidine (800 mg, 3.7 mmol) in 2 mL of DMSO were added L-proline t-butylester (660 mg, 3.7 mmol) and DIEA (1.3 mL, 7.4 mmol). The mixture was heated at 90C in a microwave for one hour. After cooling, 4-(3-carboxypropyl)piperidine hydrochloride (770 mg, 3.7 mmol) and DIEA (650 mu, 3.7 mmol) were added, and the reaction was heated at 120C for three hours. EtOAc was added and the solution was washed with IN HCl and brine, dried Na2S04), concentrated in vacuo, and purified via silica gel chromatography (0-5% MeOH/DCM) to afford Compound 29A (1.3 g, 72%). LCMS (method A): m/z 487.3 (M+H)+.

According to the analysis of related databases, 705-24-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; VENENUM BIODESIGN LLC; HUANG, Chia-Yu; MCGUINNESS, Brian F; XU, Xiaoqing; KULTGEN, Steven G.; MCMASTER, Ellen Sieber; BEASLEY, James R.; (356 pag.)WO2018/5794; (2018); A2;,
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The major producers of chemicals have been the Europe, Japan and China. Due to the growing call for a cleaner, greener environment, people will have to find innovative ways to maintain their relevance. Here is a compound 74-69-1, name is 2-Methyl-4-pyrimidinamine. This compound has unique chemical properties. The synthetic route is as follows. 74-69-1

Example 58: (R)-l-[(2-Methyl-pyrimidin-4-ylcarbamoyl)-methyl]-3-(l-phenyl- cycloheptanecarbonyloxy)-l-azonia-bicyclo[2.2.2]octane chloridea) 2-Chloro-N-(2-methyl-pyrimidin-4-yl)-acetarnideH,ISLCl 2-Methyl-pyrimidin-4-yl amine (545 mg) was suspended in DCE (5 niL) and chloroacetylchloride (0.4 mL) was added dropwise. The reaction was heated in a microwave at 8O0C for 5mins. The reaction mixture was cooled to give a solid that wa ftered, washed with dichloromethane then suspended in dichloromethane and sat. NaHCO3 (aq) was added. The organic phase was collected and the aqueous layer ext? with dichloromethane (x2). The combined organic layer was dried over sodium sulphc and concentrated. The crude product was purified by silica gel chromatography elutinj with 0-10%MeOH/dichloromethane to give the sub-titled compound as a yellow solid mg, 7.5 %).1H NMR (400 MHz, DMSO-D6): delta 1 1.16 (s, IH), 8.58 (d, IH), 7.84 (d, IH), 4.37 (s, 2.53 (s, 3H).

Statistics shows that 74-69-1 is playing an increasingly important role. we look forward to future research findings about 2-Methyl-4-pyrimidinamine.

Reference:
Patent; ASTRAZENECA AB; ARGENTA DISCOVERY LIMITED; WO2009/138707; (2009); A1;,
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130049-82-0, Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 130049-82-0, name is 3-(2-Chloroethyl)-6,7,8,9-tetrahydro-9-hydroxy-2-methyl-4H-pyrido[1,2-a]pyrimidine-4-one. This compound has unique chemical properties. The synthetic route is as follows.

Example 3 Preparation of Compound of Formula (I) PaliperidoneIn a three necked flask acetonitrile (230 ml), compound (IV) (20 g) and compound (VI) (23.3 g) were charged. To the reaction mass, potassium carbonate (18 g) and potassium iodide (0.5 g) were added. The contents were heated to 76-78 C. and maintained for 3 hours at 76-78 C. After completion of reaction, the reaction mixture was cooled to 0-5 C. and stirred for 1 hour. The solid, was filtered, washed with water (65 ml). The solid obtained was dissolved in methanol (190 ml) by heating the contents to 60-65 C., treated with activated charcoal (3.5 gm), stirred at 60-65 C. for 30 minutes. The reaction mass was filtered hot over hyflo at 60-65 C., washed with hot methanol (20 ml). Methanol was distilled completely under vacuum below 45 C. to obtain residue. Ethyl acetate (20 ml) was charged and continued distillation under vacuum to remove traces of methanol. The residue was stirred in (20 ml) ethyl acetate for 1 hour at 25-30 C. The resulting solid was filtered and washed with ethyl acetate (10 ml) and dried under vacuum at 40-45 C. for 6 hours to yield 6.5 g of paliperidone. (HPLC purity-99.5%).

While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant.we look forward to future research findings about 130049-82-0, 3-(2-Chloroethyl)-6,7,8,9-tetrahydro-9-hydroxy-2-methyl-4H-pyrido[1,2-a]pyrimidine-4-one.

Reference:
Patent; CIPLA LIMITED; US2010/298565; (2010); A1;,
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Pyrimidine – Wikipedia

504-17-6 , The common heterocyclic compound, 504-17-6, name is 4,6-Dihydroxy-2-mercaptopyrimidine, molecular formula is C4H4N2O2S, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route.

General procedure: To a mixture of an aromatic aldehyde (0.25 mmol), 2-thiobarbituric acid(0.5 mmol), ammonium acetate (0.3 mmol), [H-NMP]+[HSO4]- (12 mol%)and water (2 ml) was added. Then, ultrasonic probe was directly immersed inthe resulting mixture. The progress of the reactions was monitored by TLCuntil conversion of the starting materials was satisfactory. After completion ofthe reaction, the solvent was evaporated and the precipitate was washed withEtOH and hot water to afford the pure product. All products were identified byphysical and spectroscopic data. The synthesis of the compounds 4b and 4j wasinvestigated but unfortunately even after 24 h, only a trace amount of productwas observed by TLC, that is why we could not reported the spectroscopic dataof them.

The synthetic route of 504-17-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Naeimi, Hossein; DIdar, Asieh; Rashid, Zahra; Zahraie, Zohreh; Journal of Antibiotics; vol. 70; 7; (2017); p. 845 – 852;,
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