[ CAS No. 19178-21-3 ]

Name: 19178-21-3|2-Methyl-5,6,7,8-tetrahydroquinazolin-4-ol|97%
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3d Animation Molecule Structure of 19178-21-3

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Quality Control of [ 19178-21-3 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 19178-21-3 ]

SDS Specification

Alternatived Products of [ 19178-21-3 ]

Product Details of [ 19178-21-3 ]

CAS No. :	19178-21-3	MDL No. :	MFCD16872923
Formula :	C₉H₁₂N₂O	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	POZNQGBUFZFKPQ-UHFFFAOYSA-N
M.W :	164.20 g/mol	Pubchem ID :	135431271
Synonyms :

Calculated chemistry of [ 19178-21-3 ]

Physicochemical Properties

Num. heavy atoms :	12
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.56
Num. rotatable bonds :	0
Num. H-bond acceptors :	3.0
Num. H-bond donors :	1.0
Molar Refractivity :	46.45
TPSA :	46.01 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.02 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.0
Log Po/w (XLOGP3) :	1.81
Log Po/w (WLOGP) :	1.37
Log Po/w (MLOGP) :	1.07
Log Po/w (SILICOS-IT) :	2.26
Consensus Log Po/w :	1.7

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-2.37
Solubility :	0.703 mg/ml ; 0.00428 mol/l
Class :	Soluble
Log S (Ali) :	-2.4
Solubility :	0.66 mg/ml ; 0.00402 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.56
Solubility :	0.448 mg/ml ; 0.00273 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.38

Safety of [ 19178-21-3 ]

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
GHS Pictogram:

Application In Synthesis of [ 19178-21-3 ]

* 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 [ 19178-21-3 ]
Downstream synthetic route of [ 19178-21-3 ]

[ 19178-21-3 ] Synthesis Path-Upstream 1~7

1
[ 68965-62-8 ]
[ 124-42-5 ]
[ 19178-21-3 ]

Yield	Reaction Conditions	Operation in experiment
71%	With copper; sodium t-butanolate In N,N-dimethyl-formamide at 100℃; for 0.5 h; Microwave irradiation	General procedure: A 10 mL microwave reaction tube was charged with the appropriate β-bromo α,β-unsaturated carboxylic acid 1 (0.5mmol) and amidine hydrochloride 2 (1 mmol), together withCu powder (0.05 mmol), t-BuONa (2 mmol), and DMF (3mL). The mixture was heated to 100 °C for 30 min by microwave irradiation (CEM Discover Microwave System) at 100 W initial power. The mixture was then cooled to r.t.and filtered through a short column of silica gel (CHCl3–MeOH) to remove inorganic salts. Evaporation of the solvent gave a crude mixture that was purified by TLC [silica gel 60 GF254 (Merck), CHCl3–MeOH].

Reference： [1] Applied Organometallic Chemistry, 2012, vol. 26, # 11, p. 576 - 582,7
[2] Synlett, 2013, vol. 24, # 20, p. 2705 - 2708
[3] Synlett, 2010, # 17, p. 2611 - 2616

2
[ 124-42-5 ]
[ 19178-21-3 ]

Reference： [1] Patent: EP1142881, 2001, A1,

3
[ 105550-62-7 ]
[ 19178-21-3 ]

Reference： [1] Synthesis, 1985, # 12, p. 1148 - 1149

4
[ 124-42-5 ]
[ 1655-07-8 ]
[ 19178-21-3 ]

Reference： [1] Patent: US5234936, 1993, A,

5
[ 143-37-3 ]
[ 1655-07-8 ]
[ 19178-21-3 ]

Reference： [1] Journal of the American Chemical Society, 1952, vol. 74, p. 842
[2] Journal of the American Chemical Society, 1958, vol. 80, p. 6609,6611

6
[ 62360-62-7 ]
[ 19178-21-3 ]

Reference： [1] Tetrahedron Letters, 2014, vol. 55, # 2, p. 483 - 485

7
[ 1404219-84-6 ]
[ 19178-21-3 ]

Reference： [1] Tetrahedron Letters, 2014, vol. 55, # 2, p. 483 - 485

[ 19178-21-3 ] Synthesis Path-Downstream 1~16

1
[ 19178-21-3 ]
[ 74-88-4 ]
[ 99169-53-6 ]

Reference： [1]Patent: US2861989,1956,

2
[ 143-37-3 ]
[ 1655-07-8 ]
[ 19178-21-3 ]

Reference： [1]Journal of the American Chemical Society,1952,vol. 74,p. 842
[2]Journal of the American Chemical Society,1958,vol. 80,p. 6609,6611

3
[ 105550-62-7 ]
[ 19178-21-3 ]

Reference： [1]Synthesis,1985,p. 1148 - 1149

4
[ 19178-21-3 ]
[ 60285-09-8 ]
3-{2-[4-(4-Fluoro-benzoyl)-piperidin-1-yl]-ethyl}-2-methyl-5,6,7,8-tetrahydro-3H-quinazolin-4-one [ No CAS ]

Reference： [1]European Journal of Medicinal Chemistry,1997,vol. 32,p. 651 - 659

5
[ 19178-21-3 ]
[ 81514-10-5 ]
3-{3-[4-(4-Fluoro-phenyl)-piperazin-1-yl]-propyl}-2-methyl-5,6,7,8-tetrahydro-3H-quinazolin-4-one [ No CAS ]

Reference： [1]European Journal of Medicinal Chemistry,1997,vol. 32,p. 651 - 659

6
[ 19178-21-3 ]
[ 195507-51-8 ]
3-[2-(4-Benzoyl-piperidin-1-yl)-ethyl]-2-methyl-5,6,7,8-tetrahydro-3H-quinazolin-4-one [ No CAS ]

Reference： [1]European Journal of Medicinal Chemistry,1997,vol. 32,p. 651 - 659

7
[ 19178-21-3 ]
[ 131741-82-7 ]
3-(2-{4-[Bis-(4-fluoro-phenyl)-methylene]-piperidin-1-yl}-ethyl)-2-methyl-5,6,7,8-tetrahydro-3H-quinazolin-4-one [ No CAS ]

Reference： [1]European Journal of Medicinal Chemistry,1997,vol. 32,p. 651 - 659

9
[ 19178-21-3 ]
[ 132649-93-5 ]

Reference： [1]Patent: US2861989,1956,

10
[ 19178-21-3 ]
[ 90561-38-9 ]

Yield	Reaction Conditions	Operation in experiment
95%	With 2,3-Dimethylaniline; trichlorophosphate; In diethyl ether; water; toluene;	Part B The preparation of 4-chloro-5,6,7,8-tetrahydro-2-methylquinazoline To a mixture of 4.5 mL of phosphorus oxychloride and 20 drops of dimethylaniline in 50 mL of toluene was added 4.2 g of <strong>[19178-21-3]5,6,7,8-tetrahydro-2-methyl-4-quinazolone</strong>. The resulting mixture was refluxed for 3 hours and then cooled to room temperature. The reaction mixture was poured into a ice cold aqueous potassium carbonate. After stirring for 5 minutes the mixture was added to diethyl ether/water. The organic layer was recovered washed with brine, dried over anhydrous magnesium sulfate, filtered and evaporated to yield a yellow oil. This oil was purified on silica to yield the desired compound as a light yellow solid (4.45 g, 95%): 1 H NMR (DMSO-d6, 300 MHz) delta 2.78 (m, 2H), 2.64 (m, 2H), 2.50 (s, 3H), 1.78 (m, 4H).

Reference： [1]Patent: US5234936,1993,A

11
[ 124-42-5 ]
[ 1655-07-8 ]
[ 19178-21-3 ]

Yield	Reaction Conditions	Operation in experiment
	In ethanol;	Part A The preparation of 5,6,7,8-tetrahydro-2-methyl-4-quinazolone To 50 mL of absolute ethanol under a nitrogen atmosphere was added 5.65 g of sodium metal. After all the sodium had reacted, 20.15 g of 2-carboethoxycyclohexanone was added followed by 14.50 g of acetamidine hydrochloride. The reaction was refluxed gently overnight. The reaction was cooled to room temperature and all solvents were removed by evaporation. The pH of the residue was adjusted to 6 with dilute hydrochloric acid and refluxed briefly and allowed to cool. The resulting solid was collected. Successive crops of solid were collected by concentration of the mother liquors (13.1 g, 65%): 1 H NMR (DMSO-d6, 300 MHz) delta 12.18 (s, 1H), 2.22 (m, 2H), 2.15 (m, 2H), 2.10 (s, 3H), 1.65 (m, 4H).

Reference： [1]Patent: US5234936,1993,A

12
[ 124-42-5 ]
ethyl 4-oxotetrahydro-2H-pyran-3-carboxylate [ No CAS ]
[ 19178-21-3 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In methanol;	Example 6 2-Methyl-5,6,7,8-tetrahydro-3H-quinazolin-4-one A solution of ethyl 4-oxotetrahydropyrane-3-carboxylate (510 mg) and acetamidine hydrochloride (284 mg) in methanol (5 ml) was added with potassium carbonate (816 mg) and heated under reflux for 5 hours. The reaction mixture was cooled, then poured into water, and extracted with dichloromethane. The organic layer was dried over anhydrous magnesium sulfate and then evaporated under reducedpressure, and the residue was purified by silica gel column chromatography to obtain the above-titled product (374 mg). 1H-NMR (CDCl3) delta: 1.71-1.84 (4H, m), 2.42 (3H, s), 2.50(2H, t, J=6.2Hz), 2.61 (2H, t, J=6.2Hz). Mass (EI, m/z): 164(M+).

Reference： [1]Patent: EP1142881,2001,A1

13
[ 68965-62-8 ]
[ 124-42-5 ]
[ 19178-21-3 ]

Yield	Reaction Conditions	Operation in experiment
71%	With copper; sodium t-butanolate; In N,N-dimethyl-formamide; at 100℃; for 0.5h;Microwave irradiation;	General procedure: A 10 mL microwave reaction tube was charged with the appropriate beta-bromo alpha,beta-unsaturated carboxylic acid 1 (0.5mmol) and amidine hydrochloride 2 (1 mmol), together withCu powder (0.05 mmol), t-BuONa (2 mmol), and DMF (3mL). The mixture was heated to 100 C for 30 min by microwave irradiation (CEM Discover Microwave System) at 100 W initial power. The mixture was then cooled to r.t.and filtered through a short column of silica gel (CHCl3-MeOH) to remove inorganic salts. Evaporation of the solvent gave a crude mixture that was purified by TLC [silica gel 60 GF254 (Merck), CHCl3-MeOH].

Reference： [1]Applied Organometallic Chemistry,2012,vol. 26,p. 576 - 582,7
[2]Synlett,2013,vol. 24,p. 2705 - 2708
[3]Synlett,2010,p. 2611 - 2616

14
4-fluoro-2-methyl-5,6,7,8-tetrahydroquinazoline [ No CAS ]
[ 19178-21-3 ]

Yield	Reaction Conditions	Operation in experiment
32%	With aluminum oxide;Inert atmosphere;	General procedure: 4-Fluorotetrahydroquinazoline 3a, b (0.05 mmol) was applied tocolumn, filled with aluminium oxide (h10 cm, r 0.5 cm). The column was subsequently washed upwith petroleum ether, petroleum ether:chloroform 1:1 and chloroform until alladmixtures were eluted; then individual tetrahydroquinazolinone 5a, b was eluted by methanol:chloroform1:1.

Reference： [1]Tetrahedron Letters,2014,vol. 55,p. 483 - 485

15
[ 62360-62-7 ]
[ 19178-21-3 ]

Reference： [1]Tetrahedron Letters,2014,vol. 55,p. 483 - 485

16
[ 1404219-84-6 ]
[ 19178-21-3 ]

Reference： [1]Tetrahedron Letters,2014,vol. 55,p. 483 - 485

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[ 19178-21-3 ]

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P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
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Code	Phrase
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P320
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P321
P322
P330	Rinse mouth.
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P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
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Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
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H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
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H242	Heating may cause a fire
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H261	In contact with water releases flammable gas
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Health hazards
Code	Phrase
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H301	Toxic if swallowed
H302	Harmful if swallowed
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H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
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Environmental hazards
Code	Phrase
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H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 19178-21-3 ]

Quality Control of [ 19178-21-3 ]

Related Doc. of [ 19178-21-3 ]

Product Details of [ 19178-21-3 ]

Calculated chemistry of [ 19178-21-3 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 19178-21-3 ]

Application In Synthesis of [ 19178-21-3 ]

[ 19178-21-3 ] Synthesis Path-Upstream 1~7

[ 19178-21-3 ] Synthesis Path-Downstream 1~16

Related Functional Groups of [ 19178-21-3 ]

Alcohols

Related Parent Nucleus of [ 19178-21-3 ]

Other Aromatic Heterocycles

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 19178-21-3 ]

Related Parent Nucleus of
[ 19178-21-3 ]