Category: 1127-85-1

Some common heterocyclic compound, 1127-85-1, name is 2,4-Dichloro-5,6,7,8-tetrahydroquinazoline, molecular formula is C8H8Cl2N2, 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. 1127-85-1

EXAMPLE XIV STR44 A mixture of 2,4-dichloro-5,6,7,8-tetrahydroquinazoline ?prepared according to the procedure described by M. Botta et al., 40, Tetrahedron, (1984), 3313! (500 mg, 2.4 mmol), phenylhydrazine (270 mg, 2.5 mmol) and N,N-diisopropylethylamine (1 ml, 5.7 mmol) in THF (50 ml) was heated at reflux temperature overnight. The reaction was cooled to room temperature and phosgene (200 ml, 20% in toluene) was added slowly and stirred for an additional 10 min. The mixture was poured into water and extracted with ethyl acetate (3*50 ml). The combined organic layers were washed with brine, dried over Na2 SO4 and evaporated under reduced pressure. The residue was triturated with ethanol and filtered to afford 5-chloro-2-phenyl-7,8,9,10-tetrahydro-1,2,4-triazolo[4,3-c]quinazolin-3-one, m.p. 205-207 C.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1127-85-1, its application will become more common.

Reference:
Patent; Neurogen Corporation; US5677309; (1997); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

The chemical industry reduces the impact on the environment during synthesis 1127-85-1, name is 2,4-Dichloro-5,6,7,8-tetrahydroquinazoline, I believe this compound will play a more active role in future production and life. 1127-85-1

to stire solution of 2,4-dichloro-5,6,7,8-tetrahydroquinazoline (6.46g, 18.8 mmol) in THF(5 mL) was added (rac)-(28,38)-methyl 3-aminobicyclo[2.2.2]octane-2-carboxylate (1.99 g,20 10.8 mmol) and DIPEA (4.2 g, 5.68 mL, 32.5 mmol) and the resulting reaction mixturesolution was stirred at 70 oc for 12 h. After cooling to room temperature, the reactionmixture was poured into water (1 00 mL) and extracted with EtOAc (150 mL twice). Thecombined organic layers were washed with brine, dried over anhydrous Na2804 , filteredand concentrated in vacuo to give a crude product, which was purified by silica gel flash chomatography (0-40% EtOAc-hexane gradient) to afford the title compound ( 1 g, 26.4%yield) as white foam. MS: 350.1 [M+Ht

The chemical industry reduces the impact on the environment during synthesis 1127-85-1. I believe this compound will play a more active role in future production and life.

Reference:
Patent; SAVIRA PHARMACEUTICALS GMBH; EUROPEAN MOLECULAR BIOLOGY LABORATORY; TAN, Xuefei; ZBINDEN, Katrin Groebke; KUHN, Bernd; WANG, Lisha; LIU, Yongfu; WU, Jun; SHEN, Hong; SHI, Tianlai; (174 pag.)WO2017/133664; (2017); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

1127-85-1, name is 2,4-Dichloro-5,6,7,8-tetrahydroquinazoline, belongs to chlorides-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. 1127-85-1

Reference Example 38(R)-N-{ 1 -(2-chloro-5,6,7,8-tetrahydroquinazolin-4-yl)piperidin-3-yl}acetamide10205] (R)-(-)-3-aminopiperidine dihydrochloride (940mg, 5.42 mmol) was added to chloroform (25 ml) solution of2,4-dichloro-5,6,7,8-tetrahydroquinazoline (1 g, 4.92 mmol) prepared in Reference Example 33 and diisopropylethylamine (3.5 ml, 20.2 mmol), and then they were stirred at 60 C. overnight. Acetyl chloride (0.39 ml, 5.42 mmol) was added thereto at room temperature, and they were stirred for 2 days. The reaction solution was diluted with dichloromethane, washed with water, dried with anhydrous magnesium sulfate and concentrated under reduced pressure. The resulting residue was purified with silica gel column chromatography (n-hexane/ethyl acetate=5/1) to give the titled compound (1.2 g) as a white solid.j0206] ?H NMR (400 MHz, CD3OD) oe 7.41 (m, 1H), 7.23 (m, 1H), 7.14 (m, 1H), 4.19-3.98 (m, 5H), 3.15 (m, 2H), 2.49 (m, 1H), 2.46 (m, 3H), 2.30 (s, 3H), 2.25 (m, 1H+3H), 1.36 (m, 3H).

Statistics shows that 1127-85-1 is playing an increasingly important role. we look forward to future research findings about 2,4-Dichloro-5,6,7,8-tetrahydroquinazoline.

Reference:
Patent; YUHAN CORPORATION; SIM, Jae Young; CHA, Myung; KIM, Tae Kyun; YOON, Young Ae; KIM, Dong Hoon; (59 pag.)US2016/90374; (2016); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 1127-85-1 as follows. 1127-85-1

Reference Example 36 (S)-tert-butyl 1-(2-chloro-5,6,7,8-tetrahydroquinazolin-4-yl)pyrrolidin-3-yl-(methyl)carbamate Diisopropylethylamine (2.7 ml, 15.5 mmol) was added into chloroform (40 ml) solution of 2,4-dichloro-5,6,7,8-tetrahydroquinazoline (1.5 g, 7.39 mmol) prepared in Reference Example 33 and (3S)-(-)-3-(methylamino)-pyrrolidine (0.87 ml, 8.13 mmol), and then they were stirred at 50 C. overnight. Di-tert-butyldicarbonate (1.69 ml, 7.39 mmol) was added thereto, and they were stirred at room temperature overnight. The reaction mixture was diluted in dichloromethane, washed with water, dried with anhydrous magnesium sulfate, and then concentrated under reduced pressure. The resulting residue was purified with silica gel column chromatography (n-hexane/ethyl acetate=5/1) to give the titled compound (2.3 g) as a colorless oil. 1H NMR (400 MHz, CDCl3) delta 4.74 (s, 1H), 3.80 (m, 2H), 3.67 (m, 1H), 3.54 (m, 1H), 2.82 (s, 3H), 2.71 (m, 4H), 2.04 (m, 2H), 1.85 (m, 2H), 1.71 (m, 1H), 1.59 (m, 1H), 1.48 (s, 9H).

According to the analysis of related databases, 1127-85-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; YUHAN CORPORATION; SIM, Jae Young; CHA, Myung; KIM, Tae Kyun; YOON, Young Ae; KIM, Dong Hoon; (59 pag.)US2016/90374; (2016); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics