[ CAS No. 1193-22-2 ] {[proInfo.proName]}

Name: 1193-22-2|4-Amino-6-hydroxypyrimidine|98%
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Quality Control of [ 1193-22-2 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 1193-22-2 ]

Product Details of [ 1193-22-2 ]

CAS No. :	1193-22-2	MDL No. :	MFCD00051502
Formula :	C₄H₅N₃O	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	HFMLLTVIMFEQRE-UHFFFAOYSA-N
M.W :	111.10	Pubchem ID :	135431272
Synonyms :

Calculated chemistry of [ 1193-22-2 ]

Physicochemical Properties

Num. heavy atoms :	8
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.0
Num. rotatable bonds :	0
Num. H-bond acceptors :	2.0
Num. H-bond donors :	2.0
Molar Refractivity :	29.26
TPSA :	71.77 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-7.82 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.13
Log Po/w (XLOGP3) :	-1.18
Log Po/w (WLOGP) :	-0.64
Log Po/w (MLOGP) :	-1.26
Log Po/w (SILICOS-IT) :	0.49
Consensus Log Po/w :	-0.49

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	2.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-0.34
Solubility :	50.7 mg/ml ; 0.457 mol/l
Class :	Very soluble
Log S (Ali) :	0.17
Solubility :	163.0 mg/ml ; 1.47 mol/l
Class :	Highly soluble
Log S (SILICOS-IT) :	-1.14
Solubility :	8.07 mg/ml ; 0.0726 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.52

Safety of [ 1193-22-2 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P280-P305+P351+P338-P310	UN#:	N/A
Hazard Statements:	H302-H315-H319-H332-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 1193-22-2 ]

* 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.

Upstream synthesis route of [ 1193-22-2 ]
Downstream synthetic route of [ 1193-22-2 ]

[ 1193-22-2 ] Synthesis Path-Upstream 1~5

1
[ 1193-22-2 ]
[ 5305-59-9 ]

Reference： [1] Patent: US2005/227933, 2005, A1, . Location in patent: Page/Page column 29

2
[ 1193-22-2 ]
[ 5305-59-9 ]

Reference： [1] Patent: EP1420021, 2004, A1, . Location in patent: Page 23-24

3
[ 1193-22-2 ]
[ 91-66-7 ]
[ 5305-59-9 ]

Reference： [1] Journal of the American Chemical Society, 1958, vol. 80, p. 2182,2184

4
[ 1004-40-6 ]
[ 1193-22-2 ]

Yield	Reaction Conditions	Operation in experiment
98.4%	With ammonia; nickel; titanium(IV) oxide In water at 90℃; for 5 h;	Step two, the above 2-mercapto-4-amino-6-hydroxypyridine was added to aqueous ammonia, 2-mercapto-4-amino-6-hydroxypyridine and the mass ratio of 1:15 ammonia, the ammonia concentration was 25 percent, and then adding the active nickel and titanium oxide, 2-mercapto-4-amino-6-hydroxypyridine, activated nickel, titanium dioxide molar ratio of these three is 1: 4: 1.5, was heated to 90 deg.] C, refluxed for 5 hours, then take advantage of The active nickel and titanium dioxide were removed by hot filtration, cooled to room temperature, and a solid precipitated. The solid was washed with 30 ml of water and dried at 40 ° C to give 4-amino-6-hydroxypyrimidine in a yield of 98.4percent
64.4%	Reflux	4-Amino-6-hydroxy-2-sulfanylpyrimidine (20 g) in boiling ethanol (300 mL) was treated under stirring with Raney-Ni until the starting material disappeared. The supension was filtered while hot, the precipitate washed with hot ethanol(300 mL) and the filtrate evaporated to dryness. The residue afforded on crystallization from ethanol (ether added toturbidity) 4-amino-6-hydroxypyrimidine, m.p. 272°C. Yield, 10.0 g (64.4percent). For C4H5N3O (111.10) calculated 43.24percentC,4.54percentH, 37.82percentN; found 43.40percentC, 4.65percentH, 38.01percentN. Mass spectrum: 112 (MH+). 1H-NMR (CD3SOCD3): 4.97 s, 1H(H-5); 6.42 brs, 2H (NH2); 7.77 s, 1H (H-2); 11.41 brs, 1H (OH).

Reference： [1] Patent: CN105218554, 2016, A, . Location in patent: Paragraph 0023
[2] Journal of Medicinal Chemistry, 2002, vol. 45, # 9, p. 1918 - 1929
[3] Patent: EP1406911, 2016, B1, . Location in patent: Paragraph 00382; 00383

5
[ 1004-40-6 ]
[ 1193-22-2 ]

Reference： [1] Patent: EP1420021, 2004, A1, . Location in patent: Page 23-24

[ 1193-22-2 ] Synthesis Path-Downstream 1~14

1
[ 1193-22-2 ]
[ 77-78-1 ]
[ 1122-46-9 ]

Reference： [1]Justus Liebigs Annalen der Chemie,1958,vol. 612,p. 163,164

2
[ 1004-40-6 ]
[ 1193-22-2 ]

Yield	Reaction Conditions	Operation in experiment
	With ammonia;nickel; In water; for 2h;Heating / reflux;	4-amino-6-hydroxy-2-thiopyrimidine was treated with Raney nickel (RaNi) in water and ammonia and heated to reflux for 2 h. Purification afforded the 4-amino-6-hydroxypyrimidine, which was combined with phosphorus oxychloride and N,N-diethylaniline and heated at reflux for 4 h to give 4-amino-6-chloropyrimidine. This product was combined with diphenylborinic acid ethanolamine ester in toluene with diisopropylethylamine and heated to reflux overnight to produce the title compound.

Reference： [1]Journal of the Society of Chemical Industry,1950,vol. 69,p. 353
[2]Patent: US2005/227933,2005,A1 .Location in patent: Page/Page column 29

3
[ 1004-40-6 ]
[ 7664-41-7 ]
[ 7732-18-5 ]
Raney nickel [ No CAS ]
[ 1193-22-2 ]

Reference： [1]Justus Liebigs Annalen der Chemie,1958,vol. 612,p. 163,164

6
[ 1193-22-2 ]
[ 151965-56-9 ]
4-amino-1-[2-(diisopropylphosphonylmethoxy)-ethyl]pyrimidin-6(1H)-one [ No CAS ]
4-amino-6-[2-(diisopropylphosphonylmethoxy)ethoxy]pyrimidine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
41.1%; 26.8%		This compound (3.6 g, 33.6 mmol) in DMF (70 mL) was treated with NaH (1.36 g, 34 mmol, 60percent dispersion in paraffin oil) 0.5 h under stirring, and diisopropyl 2-chloroethoxymethylphosphonate (9.4 mL, 40.5 mmol) was added. The mixture was stirred 8 h at 80°C, filtered through celite pad and evaporated in vacuo. The residue in chloroform was purified on silica gel; elution with chloroform-ethanol (97.5:2.5) afforded 4-amino-6-[2-(diisopropylphosphonylmethoxy)ethoxy]pyrimidine which was crystallized from ethyl acetate - petroleum ether. Yield, 3.0 g (26.8percent), m.p. 112°C. For C13H24N3O5P (333.32) calculated 46.84percentC, 7.26percentH, 12.61percentN, 9.29percentP; found 46.69percentC, 7.38percentH, 12.45percentN, 9.40percentP. 1H NMR (CD3SOCD3): 1.22 d, 6 H and 1.23 d, 6 H, J(CH3,CH)=6.1 (4xCH3); 3.78 brt, 2 H, J(2',1')=4.5 (H-2'); 3.78 d, J(CH2-P)=8.4 (CH2-P); 4.31 brt, 2H, J(1',2')=4.5 (H-1'); 4.59 m, 2 H (P-OCH); 5.67 s, 1 H (H-5); 6.62 bs, 2H (NH2); 8.07 s, 1H (H-2). 13C NMR (CD3SOCD3): 64.42 (C-1'). Further elution of the crude reaction mixture on silica gel column with chloroform-ethanol (95:5) gave the oily4-amino-1-[2-(diisopropylphosphonylmethoxy)-ethyl]pyrimidin-6(1H)-one which was dried in vacuo. Yield, 4.6 g (41.1percent). This compound was treated with bromotrimethylsilane (10 mL) in acetonitrile (70 mL) overnight at room temperature.After evaporation in vacuo, the residue was treated with water (100 mL). After 10 min, conc. aqueous ammonia wasadded to alkaline reaction and the mixture was evaporated. The residue was applied on a column (100 mL) of Dowex50 X 8 and eluted with water. The main UV-absorbing fraction was evaporated and the residue was crystallized from70percent aqueous ethanol (ether added to turbidity). Yield, 2.8 g (91percent) 4-amino-1-[2-(phosphonomethoxy)ethyl]pyrimidin-6(1H)-one, m.p. 233°C. For C7H12N3O5P (249.16) calculated 33.74percentC, 4.85percentH, 16.86percentN, 12.43percentP; found 34.02percentC,4.80percentH, 16.88percentN, 12.58percentP. 1H NMR (CD3SOCD3): 3.56 d, 2H, J(CH2,P)=8.8 (CH2P); 3.64 t, 2H, J(2?,1?)=4.9 (H-2?);3.90t, 2H, J(1?,2?)=4.9 (H-1?); 5.06 s, 1 H (H-5); 6.45 brs, 2H (NH2); 6.90 brs, 2H (P-OH); 7.98 s, 1H (H-2). 13C NMR(CD3SOCD3): 44.44 (C-1?).

Reference： [1]Journal of Medicinal Chemistry,2002,vol. 45,p. 1918 - 1929
[2]Patent: EP1406911,2016,B1 .Location in patent: Paragraph 0082; 0084; 0086

7
[ 1004-40-6 ]
[ 1193-22-2 ]

Yield	Reaction Conditions	Operation in experiment
98.4%	With ammonia; nickel; titanium(IV) oxide; In water; at 90℃; for 5h;	Step two, the above 2-mercapto-4-amino-6-hydroxypyridine was added to aqueous ammonia, 2-mercapto-4-amino-6-hydroxypyridine and the mass ratio of 1:15 ammonia, the ammonia concentration was 25 percent, and then adding the active nickel and titanium oxide, 2-mercapto-4-amino-6-hydroxypyridine, activated nickel, titanium dioxide molar ratio of these three is 1: 4: 1.5, was heated to 90 deg.] C, refluxed for 5 hours, then take advantage of The active nickel and titanium dioxide were removed by hot filtration, cooled to room temperature, and a solid precipitated. The solid was washed with 30 ml of water and dried at 40 ° C to give 4-amino-6-hydroxypyrimidine in a yield of 98.4percent
64.4%	With ethanol;Reflux;	4-Amino-6-hydroxy-2-sulfanylpyrimidine (20 g) in boiling ethanol (300 mL) was treated under stirring with Raney-Ni until the starting material disappeared. The supension was filtered while hot, the precipitate washed with hot ethanol(300 mL) and the filtrate evaporated to dryness. The residue afforded on crystallization from ethanol (ether added toturbidity) 4-amino-6-hydroxypyrimidine, m.p. 272°C. Yield, 10.0 g (64.4percent). For C4H5N3O (111.10) calculated 43.24percentC,4.54percentH, 37.82percentN; found 43.40percentC, 4.65percentH, 38.01percentN. Mass spectrum: 112 (MH+). 1H-NMR (CD3SOCD3): 4.97 s, 1H(H-5); 6.42 brs, 2H (NH2); 7.77 s, 1H (H-2); 11.41 brs, 1H (OH).

Reference： [1]Patent: CN105218554,2016,A .Location in patent: Paragraph 0023
[2]Journal of Medicinal Chemistry,2002,vol. 45,p. 1918 - 1929
[3]Patent: EP1406911,2016,B1 .Location in patent: Paragraph 00382; 00383

8
[ 1193-22-2 ]
[ 655253-93-3 ]

Yield	Reaction Conditions	Operation in experiment
23%		4-Amino-6-hydroxypyrimidine [(1.] 77 g) was stirred in aqueous sodium hydroxide (1. 5N, 12.7 [ML)] and heated to [60 C] for 30 minutes. After cooling to ambient temperature, iodine (4.04 g) was added and the mixture refluxed for 2 hours. The mixture was cooled in an ice bath, filtered, washed with ice-cold water (10 mL), dried by suction then in a vacuum oven over [PXOG] at [60 C] for 16 hours to afford the title compound as a white solid [(886] mg, 23percent); 1H NMR [(DMSO-D6)] 8 6.65 (b s, 1H), 7.76 (s, 1H), 11.34 (b s, [2H)] ; MS m/e [MT] [238.]

Reference： [1]Patent: WO2004/13141,2004,A1 .Location in patent: Page 97

9
[ 39562-17-9 ]
[ 1193-22-2 ]
(+/-)-3,4,5,8-Tetrahydro-7-methyl-5-(3-nitrophenyl)-4-oxo-pyrido[2,3-d]pyrimidine-6-carboxylic acid methyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In ethanol;	EXAMPLE 2 (+-)-3,4,5,8-Tetrahydro-7-methyl-5-(3-nitrophenyl)-4-oxo-pyrido[2,3-d]pyrimidine-6-carboxylic acid methyl ester (process b) Seventeen and 0.5 g (70 mmol) 3-nitrobenzylidene aceto-acetic methyl ester and 7.8 g (70 mmol) <strong>[1193-22-2]4-amino-6-hydroxypyrimidine</strong> are heated under reflux in 800 ml dry ethanol for 20 hours. The crystals precipitated after cooling yield, following recrystallization from ethanol, colorless needles of a mp of 289-290 C.

Reference： [1]Patent: US4677108,1987,A

10
[ 1193-22-2 ]
[ 5305-59-9 ]

Yield	Reaction Conditions	Operation in experiment
	With N,N-diethylaniline; trichlorophosphate; for 4h;Heating / reflux;	4-amino-6-hydroxy-2-thiopyrimidine was treated with Raney nickel (RaNi) in water and ammonia and heated to reflux for 2h. Purification afforded the <strong>[1193-22-2]4-amino-6-hydroxypyrimidine</strong>, which was combined with phosphorus oxychloride and N,N-diethylaniline and heated at reflux for 4h to give 4-amino-6-chloropyrimidine. This product was combined with diphenylborinic acid ethanolamine ester in toluene with diisopropylethylamine and heated to reflux overnight to produce the title compound.

Reference： [1]Patent: EP1420021,2004,A1 .Location in patent: Page 23-24

11
[ 1004-40-6 ]
[ 1193-22-2 ]

Yield	Reaction Conditions	Operation in experiment
	With ammonia; nickel; In water; for 2h;Heating / reflux;	4-amino-6-hydroxy-2-thiopyrimidine was treated with Raney nickel (RaNi) in water and ammonia and heated to reflux for 2h. Purification afforded the 4-amino-6-hydroxypyrimidine, which was combined with phosphorus oxychloride and N,N-diethylaniline and heated at reflux for 4h to give 4-amino-6-chloropyrimidine. This product was combined with diphenylborinic acid ethanolamine ester in toluene with diisopropylethylamine and heated to reflux overnight to produce the title compound.

Reference： [1]Patent: EP1420021,2004,A1 .Location in patent: Page 23-24

12
[ 1193-22-2 ]
6-amino-5-bromo-3<i>H</i>-pyrimidin-4-one [ No CAS ]

Reference： [1]European Journal of Medicinal Chemistry,2008,vol. 43,p. 1248 - 1260

13
[ 1193-22-2 ]
[ 341-92-4 ]
[ 1229607-80-0 ]

Yield	Reaction Conditions	Operation in experiment
16.48%		To a solution of 6-aminopyrimidin-4(3/-/)-one (866 mg, 7.79 mmol) in DMSO (10.0 ml.) at RT was added DBU (1.29 ml_, 8.57 mmol) and after 30 min a sol ution of 1-fluoro-4- nitronaphthalene (1.57 g, 8.18 mmol) in DMSO (3.0 ml.) was added over 2 min. The resulting mixture was maintained at RT for 2 hr and was diluted with MeOH (20 ml.) and TFA (2.0 ml.) was added. The solution was subjected to SCX capture and release and the crude product so obtained was purified by flash column chromatography (SiO2, 80 g, EtOAc in isohexane, 50- 100%, gradient elution) to afford the title compound as a yellow solid (370mg, 16.48 %); R' 3.82 min (Method 1 basic); m/z 283 (M+H)+ (ES+)

Reference： [1]Patent: WO2010/67130,2010,A1 .Location in patent: Page/Page column 84

14
[ 107-20-0 ]
[ 1193-22-2 ]
4-hydroxypyrrolo[2,3-D]pyrimidine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
89%	With sodium acetate; In water; at 70℃; for 5h;	Step three, the above-mentioned 4-amino-6-hydroxypyridine and sodium acetate added to the water quality amino-6-hydroxy-pyrimidine and water ratio of 1: 15,4- amino-6-hydroxypyridine and sodium acetate in molar ratio of 1: 4, was heated to 70 , 2- chloroacetaldehyde solution was added slowly, the concentration of the aqueous solution of 2-chloro-acetaldehyde was 30percent, 4-amino-6-hydroxypyridine and 2-chloroacetaldehyde the molar ratio of 1: 4, the reaction was stirred for 5 hours, cooled to room temperature, filtered and the solid washed with 30ml of water, 40 dried to give 4-hydroxy-pyrrolopyrimidine in 89percent yield;

Reference： [1]Patent: CN105218554,2016,A .Location in patent: Paragraph 0024

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P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
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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
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
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
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
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
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
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. 1193-22-2 ] {[proInfo.proName]}

Quality Control of [ 1193-22-2 ]

Related Doc. of [ 1193-22-2 ]

Product Details of [ 1193-22-2 ]

Calculated chemistry of [ 1193-22-2 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 1193-22-2 ]

Application In Synthesis of [ 1193-22-2 ]

[ 1193-22-2 ] Synthesis Path-Upstream 1~5

[ 1193-22-2 ] Synthesis Path-Downstream 1~14

Related Functional Groups of [ 1193-22-2 ]

Amides

Amines

Related Parent Nucleus of [ 1193-22-2 ]

Pyrimidines

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 1193-22-2 ]

Related Parent Nucleus of
[ 1193-22-2 ]