Home Cart Sign in  
Chemical Structure| 537705-06-9 Chemical Structure| 537705-06-9

Structure of 537705-06-9

Chemical Structure| 537705-06-9

*Storage: {[sel_prStorage]}

*Shipping: {[sel_prShipping]}

,{[proInfo.pro_purity]}

4.5 *For Research Use Only !

{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]} Purity: {[proInfo.pro_purity]}

Change View

Size Price VIP Price

US Stock

Global Stock

In Stock
{[ item.pr_size ]} Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price, item.vip_usd) ]}

US Stock: ship in 0-1 business day
Global Stock: ship in 5-7 days

  • {[ item.pr_size ]}

In Stock

- +

Please Login or Create an Account to: See VIP prices and availability

US Stock: ship in 0-1 business day
Global Stock: ship in 2 weeks

  • 1-2 Day Shipping
  • High Quality
  • Technical Support
Product Citations

Alternative Products

Product Details of [ 537705-06-9 ]

CAS No. :537705-06-9
Formula : C13H14N2O
M.W : 214.26
SMILES Code : NC1=CC=C(OC2=CC=C(C)N=C2)C(C)=C1
MDL No. :MFCD06657266

Safety of [ 537705-06-9 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of [ 537705-06-9 ]

* 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.

  • Downstream synthetic route of [ 537705-06-9 ]

[ 537705-06-9 ] Synthesis Path-Downstream   1~4

  • 1
  • [ 537705-06-9 ]
  • [ 98556-31-1 ]
  • [ 537705-10-5 ]
YieldReaction ConditionsOperation in experiment
76% In 1,2-dichloro-ethane; tert-butyl alcohol; for 6h;Heating / reflux; A mixture OF 3-METHYL-4-(6-METHYL-PYRIDIN-3-YLOXY)-PHENYLAMINE (4.96 g, 23.18 MMOL), 4-Chloro-6-iodo-quinazoline 604 g, 22.06 mmol) in tBuOH (60 mL) and DCE (60 mL) was refluxed for 6 hours. The reaction was cooled to 0C and the solid product (8. 44 g, 76%) was isolated by filtration and washed with cold CHACLA (50 mL)
76% In 1,2-dichloro-ethane; tert-butyl alcohol; for 6h;Heating / reflux; Step C: (6-iodo-quinazolin-4-yl)-[3-methyl-4-(6-methyl-pyridin-3-yloxy)-phenyl]-amine hydrochloride A mixture of 3-methyl-4-(6-methyl-pyridin-3-yloxy)-phenylamine (4.96 g, 23.18 mmol), 4-Chloro-6-iodo-quinazoline 604 g, 22.06 mmol) in tBuOH (60 mL) and DCE (60 mL) was refluxed for 6 hours. The reaction was cooled to 0 C. and the solid product (8.44 g, 76%) was isolated by filtration and washed with cold CH2Cl2 (50 mL).
  • 2
  • [ 537705-06-9 ]
  • [ 98556-31-1 ]
  • [ 537705-05-8 ]
YieldReaction ConditionsOperation in experiment
98% In tetrahydrofuran; at 56℃; for 2.66667h; A 3 neck round bottom flask was fitted with a mechanical stirrer and kept under N2. The flask was charged with the 6-IODO-4-CHLOROQUINAZOLINE (10.0 g, 34.43 mol) and dry THF (35 ML). Thereafter, 3-METHYL-4- (6-METHYL-PYRIDINE-3-YLOXY)-PHENYLAMINE (7.38 g, 34.43 MMOL) and dry THF (45 ml) were added and the yellow suspension was heated to reflux. After 15 minutes most of the reactants went into solution and a fine yellow suspension was obtained. After 25 min, the internal temperature of the reaction mixture was 56C, and precipitation of the desired product started. Heating was continued for a further 2 hours and the reaction mixture was allowed to cool to room temperature while remaining in the oil bath. Yellow crystals were collected by filtration, washed with cold (0C) THF (1 x 10 ml) and dried at 50C, p < 200 mbar. The title compound was obtained as light yellow crystals (15.75g, 98%). Rf = 0.45 (EtOAc/MeOH = 9/1).'H NMR (CDCI3, 300 MHz): 8 = 11.40 (br, s, 1H, NH), 9.29 (d, J = Hz, 1H, H-2), 8.91 (S, 1H, H-2"), 8.36-8. 32 (m, 2H, H-7, H-8), 7.74-7. 73 (m, 2H, H-4", H-5), 7.62 (dd, J, = 8.7Hz, J2 = 2.6Hz, 1 H, H-5") 7.49-7. 46 (m, 2H, H-6', H-5), 7.06 (d, J = 8.7Hz, 1 H, H-2'), 2.54 (s, 3H, CH3), 2.26 (s, 3H, CH3). 13C NMR (CDCI3 + D6-DMSO, 75 MHz): 8 = 159.51, 153.63, 153.17, 152.82, 152.70, 145.26, 141.37, 138.01, 134.75, 134.65, 131.05, 129.10, 128.74, 126.77, 124.86, 124.43, 120.41, 116. 98, 94.89, 23.54, 17.67. The title compound had a tR (min) of 12.13 under the following RP-HPLC conditions: Symmetry Shield RP18, 75 x 4.6 mm; Flow 1.0 mL/min ; 205/210/220/245 nm; Temp. 25C ; Injection Volume: 10 uL OF A CA. 0.5% solution in ACN/H20 9/1; Eluent : B: ACN, C: 0.01 mmol NH40Ac in H20 pH = 6.0 ; and Gradient: 0 min: B = 30%, C = 70 %; and 20 min: B = 85%, C =15%.
98% In tetrahydrofuran; at 56℃; for 2.5h;Heating / reflux; Synthesis of 6-Iodo-[3-methyl-4-(6-methyl-pyridine-3-yloxy)-phenylamino]-quinazoline A 3 neck round bottom flask was fitted with a mechanical stirrer and kept under N2. The flask was charged with the 6-iodo-4-chloroquinazoline (10.0 g, 34.43 mol) and dry THF (35 ml). Thereafter, 3-methyl-4-(6-methyl-pyridine-3-yloxy)-phenylamine (7.38 g, 34.43 mmol) and dry THF (45 ml) were added and the yellow suspension was heated to reflux. After 15 minutes most of the reactants went into solution and a fine yellow suspension was obtained. After 25 minutes, the internal temperature of the reaction mixture was 56 C., and precipitation of the desired product started. Heating was continued for a further 2 hours and the reaction mixture was allowed to cool to room temperature while remaining in the oil bath. Yellow crystals were collected by filtration, washed with cold (0 C.) THF (1*10 ml) and dried at 50 C., p<200 mbar. The title compound was obtained as light yellow crystals (15.75 g, 98%). Rf=0.45 (EtOAc/MeOH=9/1). 1H NMR (CDCl3, 300 MHz): δ=11.40 (br, s, 1H, N), 9.29 (d, J=Hz, 1H, -2), 8.91 (s, 1H, -2"), 8.36-8.32 (m, 2H, -7, -8), 7.74-7.73 (m, 2H, -4", -5), 7.62 (dd, J1=8.7 Hz, J2=2.6 Hz, 1H, H-5") 7.49-7.46 (m, 2H, H-6', H-5), 7.06 (d, J=8.7 Hz, 1H, -2'), 2.54 (s, 3H, C3), 2.26 (s, 3H, C3). 13C NMR (CDCl3+D6-DMSO, 75 MHz): δ=159.51, 153.63, 153.17, 152.82, 152.70, 145.26, 141.37, 138.01, 134.75, 134.65, 131.05, 129.10, 128.74, 126.77, 124.86, 124.43, 120.41, 116.98, 94.89, 23.54, 17.67.
93% In isopropyl alcohol; at 80℃; for 2h; General procedure: To a solution of compound 12 (5.8 g, 20 mmol) in i-PrOH was added anilines (22 mmol) at room temperature (RT). Then the reaction mixture was heated to 80 C for 2 h. After the start material was completed, the mixture was filtered through celite, and the cake was washed by i-PrOH, then dried to obtain the desired compound 13a-f.
In isopropyl alcohol; for 12h;Reflux; Step C: N-(4-(6-methylpyridin-3-yloxy)-3-methylphenyl)-6-iodoquinazolin-4-amine(compound 12.3)[0141] 4-(6-methylpyridin-3-yloxy)-3-methylbenzenamine (812 mg, 3.79 mmol) and 4- chloro-6-iodo-quinazoline (I g, 3.4mmol) were dissolved in isopropanol (50 ml). The reaction mixture was refluxed for 12 hours. The solid product was collected by filtration, washed with cold isopropanol (10 mL) and ether (20 mL), and air dried to afford 1.1 g of the clean desired material.

  • 3
  • [ 537705-06-9 ]
  • [ 98556-31-1 ]
  • [ 383432-38-0 ]
 

Historical Records

Technical Information

Categories