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Chemical Structure| 66655-67-2 Chemical Structure| 66655-67-2

Structure of 66655-67-2

Chemical Structure| 66655-67-2

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Product Details of [ 66655-67-2 ]

CAS No. :66655-67-2
Formula : C8H8N2O
M.W : 148.16
SMILES Code : O=C1NC2=C(C=CC=C2)CN1
MDL No. :MFCD03425132
InChI Key :CTOUNZIAEBIWAW-UHFFFAOYSA-N
Pubchem ID :12360756

Safety of [ 66655-67-2 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H332-H335
Precautionary Statements:P261-P280-P305+P351+P338

Computational Chemistry of [ 66655-67-2 ] Show Less

Physicochemical Properties

Num. heavy atoms 11
Num. arom. heavy atoms 6
Fraction Csp3 0.12
Num. rotatable bonds 0
Num. H-bond acceptors 1.0
Num. H-bond donors 2.0
Molar Refractivity 48.84
TPSA ?

Topological Polar Surface Area: Calculated from
Ertl P. et al. 2000 J. Med. Chem.

41.13 Ų

Lipophilicity

Log Po/w (iLOGP)?

iLOGP: in-house physics-based method implemented from
Daina A et al. 2014 J. Chem. Inf. Model.

1.26
Log Po/w (XLOGP3)?

XLOGP3: Atomistic and knowledge-based method calculated by
XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry

0.89
Log Po/w (WLOGP)?

WLOGP: Atomistic method implemented from
Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.

0.22
Log Po/w (MLOGP)?

MLOGP: Topological method implemented from
Moriguchi I. et al. 1992 Chem. Pharm. Bull.
Moriguchi I. et al. 1994 Chem. Pharm. Bull.
Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.

1.07
Log Po/w (SILICOS-IT)?

SILICOS-IT: Hybrid fragmental/topological method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

1.23
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

0.93

Water Solubility

Log S (ESOL):?

ESOL: Topological method implemented from
Delaney JS. 2004 J. Chem. Inf. Model.

-1.72
Solubility 2.8 mg/ml ; 0.0189 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Very soluble
Log S (Ali)?

Ali: Topological method implemented from
Ali J. et al. 2012 J. Chem. Inf. Model.

-1.34
Solubility 6.8 mg/ml ; 0.0459 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Very soluble
Log S (SILICOS-IT)?

SILICOS-IT: Fragmental method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

-2.92
Solubility 0.178 mg/ml ; 0.0012 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Soluble

Pharmacokinetics

GI absorption?

Gatrointestinal absorption: according to the white of the BOILED-Egg

High
BBB permeant?

BBB permeation: according to the yolk of the BOILED-Egg

No
P-gp substrate?

P-glycoprotein substrate: SVM model built on 1033 molecules (training set)
and tested on 415 molecules (test set)
10-fold CV: ACC=0.72 / AUC=0.77
External: ACC=0.88 / AUC=0.94

No
CYP1A2 inhibitor?

Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.83 / AUC=0.90
External: ACC=0.84 / AUC=0.91

No
CYP2C19 inhibitor?

Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.80 / AUC=0.86
External: ACC=0.80 / AUC=0.87

No
CYP2C9 inhibitor?

Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set)
and tested on 2075 molecules (test set)
10-fold CV: ACC=0.78 / AUC=0.85
External: ACC=0.71 / AUC=0.81

No
CYP2D6 inhibitor?

Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set)
and tested on 1068 molecules (test set)
10-fold CV: ACC=0.79 / AUC=0.85
External: ACC=0.81 / AUC=0.87

No
CYP3A4 inhibitor?

Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set)
and tested on 2579 molecules (test set)
10-fold CV: ACC=0.77 / AUC=0.85
External: ACC=0.78 / AUC=0.86

No
Log Kp (skin permeation)?

Skin permeation: QSPR model implemented from
Potts RO and Guy RH. 1992 Pharm. Res.

-6.57 cm/s

Druglikeness

Lipinski?

Lipinski (Pfizer) filter: implemented from
Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev.
MW ≤ 500
MLOGP ≤ 4.15
N or O ≤ 10
NH or OH ≤ 5

0.0
Ghose?

Ghose filter: implemented from
Ghose AK. et al. 1999 J. Comb. Chem.
160 ≤ MW ≤ 480
-0.4 ≤ WLOGP ≤ 5.6
40 ≤ MR ≤ 130
20 ≤ atoms ≤ 70

None
Veber?

Veber (GSK) filter: implemented from
Veber DF. et al. 2002 J. Med. Chem.
Rotatable bonds ≤ 10
TPSA ≤ 140

0.0
Egan?

Egan (Pharmacia) filter: implemented from
Egan WJ. et al. 2000 J. Med. Chem.
WLOGP ≤ 5.88
TPSA ≤ 131.6

0.0
Muegge?

Muegge (Bayer) filter: implemented from
Muegge I. et al. 2001 J. Med. Chem.
200 ≤ MW ≤ 600
-2 ≤ XLOGP ≤ 5
TPSA ≤ 150
Num. rings ≤ 7
Num. carbon > 4
Num. heteroatoms > 1
Num. rotatable bonds ≤ 15
H-bond acc. ≤ 10
H-bond don. ≤ 5

1.0
Bioavailability Score?

Abbott Bioavailability Score: Probability of F > 10% in rat
implemented from
Martin YC. 2005 J. Med. Chem.

0.55

Medicinal Chemistry

PAINS?

Pan Assay Interference Structures: implemented from
Baell JB. & Holloway GA. 2010 J. Med. Chem.

0.0 alert
Brenk?

Structural Alert: implemented from
Brenk R. et al. 2008 ChemMedChem

0.0 alert: heavy_metal
Leadlikeness?

Leadlikeness: implemented from
Teague SJ. 1999 Angew. Chem. Int. Ed.
250 ≤ MW ≤ 350
XLOGP ≤ 3.5
Num. rotatable bonds ≤ 7

No; 1 violation:MW<1.0
Synthetic accessibility?

Synthetic accessibility score: from 1 (very easy) to 10 (very difficult)
based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties,
trained on 12'782'590 molecules and tested on 40 external molecules (r2 = 0.94)

1.75

Application In Synthesis of [ 66655-67-2 ]

* 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 [ 66655-67-2 ]

[ 66655-67-2 ] Synthesis Path-Downstream   1~33

  • 1
  • [ 75-44-5 ]
  • [ 4403-69-4 ]
  • [ 66655-67-2 ]
  • 2
  • [ 66655-67-2 ]
  • [ 106-96-7 ]
  • [ 131637-17-7 ]
  • 5
  • [ 868-84-8 ]
  • [ 4403-69-4 ]
  • [ 66655-67-2 ]
  • 6
  • <(2-hydroxyimino-methyl)-phenyl>-carbamic acid ethyl ester [ No CAS ]
  • [ 66655-67-2 ]
  • 7
  • [ 4403-69-4 ]
  • [ 105-58-8 ]
  • [ 66655-67-2 ]
  • 8
  • [ 66655-67-2 ]
  • [ 7148-74-5 ]
  • [ 109916-28-1 ]
  • 9
  • [ 66655-67-2 ]
  • [ 131637-38-2 ]
  • 10
  • [ 66655-67-2 ]
  • [ 1575-61-7 ]
  • 6-(5-chloropentanoyl)-3,4-dihydro-2(1H)-quinazoline [ No CAS ]
YieldReaction ConditionsOperation in experiment
Reference Example 177 6-(5-Chloropentanoyl)-3,4-dihydro-2(1H)-quinazoline Using 3,4-dihydro-2(1H)-quinazoline (4.0 g) and 5-chlorovaleryl chloride (8.37 g) according to the same method as that of Reference Example 1, the title compound was obtained as colorless crystals (3.9 g) 1H NMR (200MHz, DMSO-d6) delta 1.73 (4H, m), 2.96 (2H, t, J = 7.0 Hz), 3.67 (2H, t, J = 6.4 Hz), 4.38 (2H, s), 6.83 (1H, d, J = 8.8 Hz), 7.01 (1H, s), 7.75-7.80 (2H, m), 9.44 (1H, s). MS m/z: 267 [M+H]+
  • 11
  • [ 66655-67-2 ]
  • [ 100-85-6 ]
  • [ 107-02-8 ]
  • [ 329790-60-5 ]
YieldReaction ConditionsOperation in experiment
59% In methanol; water; ethyl acetate; Example 3 3-(2,4-dioxo-1,4-dihydro-2H-quinazolin-3-yl)propionaldehyde Benzoylene urea (4.0 g, 24.7 mmol), Triton B (40 wt % in methanol) (11.0 mL, 24.7 mmol), water (80 mL) and methanol (400 mL) were combined at ambient temperature and stirred vigorously for 15 minutes. (until all the solids had gone into solution). To this colorless solution, acrolein (1.7 mL, 24.7 mmol) in methanol (20 mL) was added dropwise over 5 minutes. to give a yellow solution. The reaction was then heated to 55 C and stirred for 2 hours. and then at room temperature for approximately 16 hours. The yellow solution was concentrated to give a yellow oil which was taken up in ethyl acetate (25 mL) and water (50 mL). The aqueous layer was extracted again with ethyl acetate (25 mL). The organic layers were combined, washed with 1N HCl (20 mL), water (20 mL), saturated sodium bicarbonate solution (20 mL) and brine (20 mL), the organic layer was dried over magnesium sulfate and concentrated to give 3-[2,4-dioxo-1,4-dihydro-2H-quinazolin-3-yl]propionaldehyde as a yellow foam (3.2 g, 59%) which was used without further purification. The NMR data showed a purity of ~70%. NMR CDCl3 delta 9.85 (s, 1H), 8.10-8.06 (m, 1H), 7.63-7.57 (m, 1H), 7.24-7.19 (m, 1H), 7.13-7.07 (m, 1H), 4.44-4.40 (m, 2H), 2.85 (dt, 2H, J1,2=2 Hz, J1,3=7 Hz); MS=219 (p+1).
59% In hydrogenchloride; methanol; water; ethyl acetate; Example 5 Preparation of 3-[2,4-Dioxo-1,4-dihydro-2H-quinazolin-3-yl]propionaldehyde Benzoylene urea (4.0 g, 24.7 mmol), Triton B (40 wt % in methanol) (11.0 mL, 24.7 mmol), water (80 mL) and methanol (400 mL) were combined at ambient temperature and stirred vigorously for 15 minutes. (until all the solids had gone into solution). To this colorless solution, acrolein (1.7 mL, 24.7 mmol) in methanol (20 mL) was added dropwise over 5 minutes. to give a yellow solution. The reaction was then heated to 55 C. and stirred for 2 hours. and then at room temperature for approximately 16 hours. The yellow solution was concentrated to give a yellow oil which was taken up in ethyl acetate (25 mL) and water (50 mL). The aqueous layer was extracted again with ethyl acetate (25 mL). The organic layers were combined, washed with IN HCl (20 mL), water (20 mL), saturated sodium bicarbonate solution (20 mL) and brine (20 mL), the organic layer was dried over magnesium sulfate and concentrated to give 3-[2,4-dioxo-1,4-dihydro-2H-quinazolin-3-yl]propionaldehyde as a yellow foam (3.2 g, 59%) which was used without further purification. The NMR data showed a purity of 70%. NMR CDCl3 delta 9.85 (s, 1H), 8.10-8.06 (m, 1H), 7.63-7.57 (m, 1H), 7.24-7.19 (m, 1H), 7.13-7.07 (m, 1H), 4.44-4.40 (m, 2H), 2.85 (dt, 2H, J1,2=2 Hz, J1,3=7 Hz); MS=219 (p+1).
  • 12
  • [ 66655-67-2 ]
  • [ 155967-29-6 ]
  • [ 6674-22-2 ]
  • [ 134186-64-4 ]
  • [ 155967-82-1 ]
YieldReaction ConditionsOperation in experiment
10.4% In N-methyl-acetamide; water; i) Synthesis of 1,3-bis[3-(4-pyridylthio)propyl]-quinazoline-2,4(1H,3H)-dione To a solution of 1.62 g (10 mmol) of benzoylene urea and 1.88 g (10 mmol) of 4-(3-chloropropylthio)pyridine in 50 ml of dimethylformamide, 1.65 ml (11 mmol) of 1,8-diazabicyclo[5.4.0]-7-undecene was added, and the mixture was stirred at 80 C. for 16 hours. After cooling, water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was dried and the solvent was distilled off. The residue was purified by column chromatography (eluent: ethyl acetate/ethanol =25:1 to 10:1 to 2:1). First, 0.973 g of 3-[3-(4-pyridylthio)propyl]quinazoline-2,4-(1H,3H)-dione (31.1% yield, pale yellow crystals) was obtained, and then, 0.487 g of the desired product was obtained (10.4% yield, yellow oil). NMR (200 MHz, CDCl3) delta: 2.04-2.24 (4H, m), 3.02-3.16 (4H, m), 4.27-4.35 (4H, m), 7.08-7.30 (6H, m), 7.62 (1H, ddd, J=1.8, 7.0, 7.2 Hz), 8.23 (1H, dd, J=1.6, 8.0 Hz), 8.35-8 41 (4H, m).
  • 13
  • [ 66655-67-2 ]
  • [ 625-36-5 ]
  • [ 178164-96-0 ]
YieldReaction ConditionsOperation in experiment
95.3% aluminium chloride; In dichloromethane; Example 6 6-(3-Chloro-1-oxopropyl)-<strong>[66655-67-2]1,2,3,4-tetrahydroquinazolin-2-one</strong> 20 g of aluminium chloride (0.15 mol) are taken up in 100 ml of dichloromethane. 7.43 g of <strong>[66655-67-2]1,2,3,4-tetrahydroquinazolin-2-one</strong> (0.05 mol) are added in portions with stirring at a maximum of 20 C. The reaction mixture thus obtained is subsequently stirred for 30 minutes. A solution consisting of 6.98 g of 3-chloropropionyl chloride (0.055 mol) and 50 ml of dichloromethane is then added dropwise with stirring at a temperature of at most 25 C. and the mixture is subsequently stirred for a further hour. After completion of the reaction, the reaction mixture obtained is stirred into 300 g of ice, and the precipitate is filtered off with suction and washed with plenty of water and small amounts of methanol. The reaction forms a slightly more polar product than the starting material, which can be separated by thin-layer chromatography using an eluent consisting of chloroform and methanol in the mixture ratio 95:5. Yield: 11.37 g of 6-(3-chloro-1-oxopropyl)-<strong>[66655-67-2]1,2,3,4-tetrahydroquinazolin-2-one</strong> (95.3% of theory); m.p: >270 C.
  • 14
  • [ 66655-67-2 ]
  • [ 44806-45-3 ]
  • 6-(3-Carboxy-propionyl)-3,4-dihydro-2(1H)-quinazolinone [ No CAS ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride;aluminium trichloride; In carbon disulfide; Step 1. 6-(3-Carboxy-propionyl)-<strong>[66655-67-2]3,4-dihydro-2(1H)-quinazolinone</strong> 3,4-Dihydro-2(1H)-quinazolinone (4.8 g) is added to a stirred suspension of anhydrous aluminum chloride (21.7 g) in carbon disulfide (100 ml) under nitrogen. Methyl succinyl chloride (4.9 g) is added dropwise to the stirred suspension, the reaction mixture refluxed for about 70 hours, cooled to RT and the liquid phase decanted. The residue is treated with ice and 6N HCl, filtered, and the solid air dried, affording the desired crude product, M.P. 176-180 C., which is used in the next step without further purification.
  • 15
  • [ 22118-09-8 ]
  • [ 66655-67-2 ]
  • 6-(Bromoacetyl)-3,4-dihydro-2(1H)-quinazolinone [ No CAS ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride;aluminium trichloride; In carbon disulfide; Step 1 6-(Bromoacetyl)-<strong>[66655-67-2]3,4-dihydro-2(1H)-quinazolinone</strong> Bromoacetyl chloride (6.2 g) is added dropwise to a stirring mixture of <strong>[66655-67-2]3,4-dihydro-2(1H)-quinazolinone</strong> (2.6 g) and anhydrous aluminum chloride (6.3 g) in carbon disulfide (60 ml). The reaction mixture is stirred under reflux for 4.5 hours, the carbon disulfide decanted, and the residue treated with HCl (6N). The resulting solid is poured into ice water, filtered, the filtered solid washed with water and dried in vacuo, affording the desired product, which is used in the next step without further purification.
  • 16
  • [ 66655-67-2 ]
  • [ 563-76-8 ]
  • [ 109916-28-1 ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride;aluminium trichloride; In carbon disulfide; Step 1 6-(2-Bromopropionyl)-<strong>[66655-67-2]3,4-dihydro-2(1H)-quinazolinone</strong> 2-Bromopropionyl bromide (10.6 g) is added dropwise to a stirring mixture of <strong>[66655-67-2]3,4-dihydro-2(1H)-quinazolinone</strong> (3.2 g) and anhydrous aluminum chloride (7.9 g) in carbon disulfide (60 ml). The reaction mixture is refluxed for four hours, the carbon disulfide decanted and the residue treated with aqueous hydrochloric acid (6N). The acidic residue is poured into ice water, and the precipitate filtered, washed with water and dried, affording the desired product as a solid, which is used in the next step without further purification.
  • 17
  • [ 66655-67-2 ]
  • [ 82923-97-5 ]
  • 6-(3-Carbomethoxy-2-methyl-propionyl)-3,4-dihydro-2(1H)-quinazolinone [ No CAS ]
YieldReaction ConditionsOperation in experiment
aluminium trichloride; In carbon disulfide; diethyl ether; water; Step 1. 6-(3-Carbomethoxy-2-methyl-propionyl)-<strong>[66655-67-2]3,4-dihydro-2(1H)-quinazolinone</strong> 3,4-Dihydro-2(1H)-quinazolinone (3.6 g) is added to a stirred suspension of anhydrous aluminum chloride (16.5 g) in carbon disulfide (120 ml) under nitrogen. 3-Carbomethoxy-2-methyl-propionyl chloride (4 g) is added dropwise to the stirred suspension, and the reaction mixture refluxed for about 18 hours, cooled to RT and further cooled to 0 C. in an ice bath. The liquid phase is decanted and ice and cold water slowly added to the residue. The aqueous mixture is filtered and the filtered solid suspended and stirred in the anhydrous diethyl ether overnight. The suspension is filtered and the filtered solid used in the next step without further purification.
aluminium trichloride; In carbon disulfide; diethyl ether; water; Step 1. 6-(3-Carbomethoxy-2-methyl-propionyl)-<strong>[66655-67-2]3,4-dihydro-2(1H)-quinazolinone</strong> 3,4-Dihydro-2(1H)-quinazolinone (3.6 g) is added to a stirred suspension of anhydrous aluminum chloride (16.5 g) in carbon disulfide (120 ml) under nitrogen. 3-Carbomethoxy-2-methyl-propionyl chloride (4 g) is added dropwise tothe stirred suspension, and the reaction mixture refluxed for about 18 hours, cooled to RT and further cooled to 0 C. in an ice bath. The liquid phase is decanted and ice and cold water slowly added to the residue. The aqueous mixture is filtered and the filtered solid suspended and stirred in the anhydrous diethyl ether overnight. The suspension is filtered and the filtered solid used in the next step without further purification.
  • 18
  • [ 124-38-9 ]
  • [ 4403-69-4 ]
  • [ 66655-67-2 ]
  • 19
  • [ 1269142-23-5 ]
  • [ 66655-67-2 ]
  • [ 1196-38-9 ]
  • 20
  • C17H17N3O2 [ No CAS ]
  • [ 66655-67-2 ]
  • [ 1196-38-9 ]
  • 21
  • [ 4403-69-4 ]
  • [ 66655-67-2 ]
  • 22
  • [ 162046-50-6 ]
  • [ 66655-67-2 ]
  • 23
  • [ 103-71-9 ]
  • [ 4403-69-4 ]
  • [ 66655-67-2 ]
  • 24
  • [ 32315-10-9 ]
  • [ 4403-69-4 ]
  • [ 66655-67-2 ]
YieldReaction ConditionsOperation in experiment
99% In tetrahydrofuran;Inert atmosphere; Triphosgene (3.31 g, 12.3 mmol) was added toa solution of 2-(aminomethyl)aniline (1.50 g, 12.3 mmol) in 30 ml THF under a nitrogenatmosphere. After precipitation of a colorless solid, stirring was continued for 30 minbefore water was added. The solution was extracted several times with ethyl acetate. Thecombined organic layers were washed with brine and dried over anhydrous MgSO4 toafford 10b (1.80 g, 12.2 mmol, 99 %) as colorless solid. 1H-NMR (500 MHz, DMSO-d6):delta = 4.30 (s, 2H), 6.75-6.77 (m, 2H), 6.84 (ddd, 3J = 3J = 7.4 Hz, 4J = 1.9 Hz, 1H), 7.06 (d,3J = 7.3 Hz, 1H), 7.09 (dd, 3J = 3J = 7.7 Hz, 1H), 8.98 (s, 1H). 13C-NMR (125 MHz,DMSO-d6): delta = 42.4, 113.4, 118.0, 120.8, 125.5, 127.4, 138.0, 154.5.
  • 25
  • [ 66655-67-2 ]
  • [ 1246765-38-7 ]
YieldReaction ConditionsOperation in experiment
50% With N-Bromosuccinimide; In N,N-dimethyl-formamide; at 0℃; for 2.0h; A solution of N-bromosuccinimide(2.26 g, 12.7 mmol) in 30 ml dry DMF was added drop wise to a solution of 10b (1.79 g,12.1 mmol) in 35 ml dry DMF at 0 C. The mixture was stirred at 0 C for 2 h. Waterwas added and the solution was extracted with ethyl acetate. The organic layer waswashed with brine, and then dried over anhydrous MgSO4. The resulting yellow solidwas purified by crystallization from acetone to afford 10a (1.37 g, 6.00 mmol, 50 %) aswhite solid. 1H-NMR (500 MHz, DMSO-d6): delta = 4.29 (s, 2H), 6.71 (d, 3J = 8.2 Hz, 1H),6.87 (s, 1H), 7.27 (dd, 3J = 8.4 Hz, 4J = 2.3 Hz, 1H), 7.29 (s, 1H), 9.13 (s, 1H). 13C-NMR(125 MHz, DMSO-d6): delta = 41.9, 112.0, 115.3, 120.7, 128.2, 130.1, 137.5, 154.1.
  • 26
  • [ 66655-67-2 ]
  • 6-(pyridin-3-yl)-3,4-dihydroquinazolin-2(1H)-one [ No CAS ]
  • 27
  • [ 66655-67-2 ]
  • 6-(isoquinolin-4-yl)-3,4-dihydroquinazolin-2(1H)-one [ No CAS ]
  • 28
  • [ 4403-69-4 ]
  • [ 13939-06-5 ]
  • [ 66655-67-2 ]
YieldReaction ConditionsOperation in experiment
12% With copper diacetate; palladium diacetate; 1,8-diazabicyclo[5.4.0]undec-7-ene; In 1,4-dioxane; at 95℃; General procedure: The reaction was performed in a double-chamber system [67,68]. Amine/amines, Pd(OAc)2(0.05 equiv.) and Cu(OAc)2 (0.5 equiv.) were added to the reaction chamber and dissolved in1,4-dioxane (2 mL). In the CO-chamber was Mo(CO)6 (200 mg) dissolved in 1,4-dioxane (2 mL).After capping of the system, 1,8-diazabicyclo[5.4.0]undec-7-ene was added to the CO-chamber.The double-chamber system was positioned in a Dry-Syn heating block and heated to 95 C. Aftercompletion of the reaction, the reaction mixture was filtered through a short silica plug before flashcolumn chromatography.
  • 29
  • [ 24424-99-5 ]
  • [ 4403-69-4 ]
  • [ 66655-67-2 ]
  • 30
  • [ 66655-67-2 ]
  • [ 4637-24-5 ]
  • [ 19270-60-1 ]
YieldReaction ConditionsOperation in experiment
91.8% In N,N-dimethyl-formamide; at 80℃; for 2.0h; To <strong>[66655-67-2]3,4-dihydroquinazoline-2(1H)-one</strong> (1.7 g, 11.6 mmol)N,N-dimethylformamide dimethyl acetal (5.5 g, 46.3 mmol) was added dropwise to the DMF solution (10 ml), and the mixture was reacted at 80 C for 2 h.Water (28 ml) and ethyl acetate (15 ml) were added, and the mixture was evaporated, evaporated, evaporated, evaporated, evaporated Concentrated to a crude product,The crude product was separated by column chromatography (eluent: petroleum ether: ethyl acetate = 10:1)The yield relative to <strong>[66655-67-2]3,4-dihydroquinazoline-2(1H)-one</strong> was 91.8%.The product purity is 99.6%(mass fraction)
  • 31
  • [ 66655-67-2 ]
  • [ 1188-33-6 ]
  • 1-ethyl-3,4-dihydroquinazoline-2(1H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
89.8% In N,N-dimethyl-formamide; at 80℃; for 2.0h; To a solution of <strong>[66655-67-2]3,4-dihydroquinazoline-2(1H)-one</strong> (0.3 g, 2.0 mmol) in DMF (4 mL)N,N-dimethylformamide diethyl acetal (1.0 g, 8.2 mmol) was added dropwise.The reaction was carried out at 80 C for 2 h.Water (10 ml) and ethyl acetate (10 ml) were added.The organic layer was combined, washed with brine, dried over anhydrous sodium sulfateThe filtrate was concentrated under reduced pressure to give a crude material.Ethyl acetate = 10:1) separation,A white solid (0.32 g, yield 89.8%) was obtained.Product purity is 99.4%(mass fraction)
  • 32
  • [ 66655-67-2 ]
  • [ 18503-89-4 ]
  • 1-isopropyl-3,4-dihydroquinazoline-2(1H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
84.2% In N,N-dimethyl-formamide; at 80℃; for 2.0h; To <strong>[66655-67-2]3,4-dihydroquinazoline-2(1H)-one</strong> (0.7 g, 4.7 mmol)DMF solution (4ml)N,N-dimethylformamide diisopropyl acetal (3.2 g, 27.2 mmol) was added dropwise.The reaction was carried out at 80 C for 2 h.Add water (18 ml) and ethyl acetate (15 ml), and separate.The aqueous layer was extracted with ethyl acetate (15×2 mL).Dry over anhydrous sodium sulfate, filter, and concentrate the filtrate under reduced pressure.The crude product was separated by column chromatography (eluent: petroleum ether: ethyl acetate = 10:1).A white solid (0.75 g, yield: 84.2%) was obtainedProduct purity is 99.4%(mass fraction)
  • 33
  • [ 124-38-9 ]
  • N,N'-Bis(trimethylsilyl)-2-aminobenzylamine [ No CAS ]
  • [ 66655-67-2 ]
 

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Technical Information

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