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[ CAS No. 35042-48-9 ] {[proInfo.proName]}

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Chemical Structure| 35042-48-9
Chemical Structure| 35042-48-9
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Product Details of [ 35042-48-9 ]

CAS No. :35042-48-9 MDL No. :MFCD13176330
Formula : C8H10N2O2 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 166.18 Pubchem ID :-
Synonyms :

Safety of [ 35042-48-9 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
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Application In Synthesis of [ 35042-48-9 ]

* 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.

  • Upstream synthesis route of [ 35042-48-9 ]
  • Downstream synthetic route of [ 35042-48-9 ]

[ 35042-48-9 ] Synthesis Path-Upstream   1~2

  • 1
  • [ 35042-48-9 ]
  • [ 1127-85-1 ]
YieldReaction ConditionsOperation in experiment
57% at 120℃; for 1 h; 2,4-dichloro-5,6,7,8-tetrahydroquinazoline (2). 5,6,7,8-tetrahydroquinazoline- 2,4(lH,3H)-dione (8.0g) was treated with phosphorousoxychloride (40 mL) and heated to 120° C for 1 h. The reaction mixture was cooled to room temperature and then excess of phosphorousoxychloride was distilled off under reduced pressure. The residue obtained was partitioned between ethyl acetate (400 mL) and water (200 mL). The organic phase was then washed with saturated NaHC03 (200 mL) followed by brine solution (200 mL). The organic phase was dried over anhydrous sodium sulfate and concentrated under reduce pressure. The residue was purified by column chromatography to obtain 2 (4.0 g, 57percent) as a yellow solid. 1H NMR (400 MHz, CDC13) δ 1.8(br s, 4H), 2.73(br s, 2H), 2.88 (br s, 2H). MS m/z (M+H): 203.1
Reference: [1] Patent: WO2014/149164, 2014, A1, . Location in patent: Paragraph 00688
[2] Journal of Medicinal Chemistry, 2011, vol. 54, # 2, p. 510 - 524
  • 2
  • [ 35042-48-9 ]
  • [ 1127-85-1 ]
YieldReaction ConditionsOperation in experiment
40% for 24 h; Reflux A suspension of 5,6,7,8-tetrahydroquinazoline-2,4-diol (2.68 g, 16.1 mmol) in POCl3 (22 mL) was stirred at reflux for one day.After completion of the reaction was confirmed by TLC,After diluting with dichloromethane, the POCl3 was concentrated under reduced pressure. The concentrated filtrate was diluted with dichloromethane,I dropped the ice slowly.The mixture was extracted with saturated Na2CO3 solution, The organic layer was dried over anhydrous Na2SO4, filtered under reduced pressure, and concentrated.The concentrated filtrate was separated and purified by silica gel column chromatography (Hex: EtOAc = 5: 1) to obtain the desired compound (1.40 g, 40percent) as a yellow solid.
5.1 g at 130℃; for 3 h; <Step 3> 2,4-dichloro-5,6,7,8-tetrahydroquinazoline
A mixture of 5,6,7,8-tetrahydroquinazolin-2,4-diol (4.85 g, 23.9 mmol) prepared in Step 2 and phosphorus oxychloride (20 ml) was stirred at 130° C. for 3 hours.
After cooling the reaction mixture to room temperature, the same was added into ice water and basified with sodium bicarbonate and sodium hydroxide.
The aqueous layer was extracted with dichloromethane, and the organic layer was dried on anhydrous magnesium sulfate and concentrated under reduced pressure.
The resulting residue was purified with silica gel column chromatography (n-hexane/ethyl acetate=15/1) to give the titled compound (5.1 g) as a white solid.
1H NMR (400 MHz, CDCl3) δ 2.89 (m, 2H), 2.74 (m, 2H), 1.88 (m, 4H).
Reference: [1] Journal of Medicinal Chemistry, 2015, vol. 58, # 24, p. 9480 - 9497
[2] Patent: KR101730790, 2017, B1, . Location in patent: Paragraph 0127; 0147-0148
[3] European Journal of Medicinal Chemistry, 1980, vol. 15, # 4, p. 317 - 322
[4] Journal of Medicinal Chemistry, 1994, vol. 37, # 22, p. 3828 - 3833
[5] Patent: US2008/132490, 2008, A1, . Location in patent: Page/Page column 20
[6] Chinese Chemical Letters, 2014, vol. 25, # 7, p. 989 - 994
[7] Patent: US2016/90374, 2016, A1, . Location in patent: Paragraph 0195; 0196
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