[ CAS No. 186435-66-5 ]

Name: 6-Amino-2-methoxypyrimidin-4-ol
Brand: Ambeed
SKU: A134719
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Quality Control of [ 186435-66-5 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 186435-66-5 ]

SDS

Alternatived Products of [ 186435-66-5 ]

Product Details of [ 186435-66-5 ]

CAS No. :	186435-66-5	MDL No. :	MFCD00068842
Formula :	C₅H₇N₃O₂	Boiling Point :	390.4±45.0°C at 760 mmHg
Linear Structure Formula :	-	InChI Key :	-
M.W :	141.13	Pubchem ID :	135404214
Synonyms :

Computed Properties of [ 186435-66-5 ]

TPSA :Topological Polar Surface Area	-	H-Bond Acceptor Count :	-
XLogP3 :	-	H-Bond Donor Count :	-
SP3 :	-	Rotatable Bond Count :	-

Safety of [ 186435-66-5 ]

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

Application In Synthesis of [ 186435-66-5 ]

Upstream synthesis route of [ 186435-66-5 ]
Downstream synthetic route of [ 186435-66-5 ]

[ 186435-66-5 ] Synthesis Path-Upstream 1~1

1
[ 52328-05-9 ]
[ 105-56-6 ]
[ 186435-66-5 ]

Yield	Reaction Conditions	Operation in experiment
80%	With sodium In methanol; water	Synthesis of 6-amino-2-methoxy-4-pyrimidone, Compound a The protocol for synthesizing compound a in the above schematic diagram was that basically as described by W. Pfleiderer (Chem. Ber., 90: 2272 (1957)). Sodium (15 g, 652 mmol) was dissolved, in small portions, in 200 ml methanol. O-Methylisourea hemisulfate (30.6 g, 248 mmol) and ethyl cyanoacetate (30 g, 265 mmol) were added to the solution. The mixture was stirred at reflux for 4.5 hours (h). The mixture was filtered, and the solid was washed carefully with methanol. The combined filtrates were evaporated to dryness, and the white solid residue was dissolved in 300 ml of hot water. After neutralization with acetic acid to pH 7, the solid was filtered, washed with water, and dried to give 28 g (80percent) of product as a white solid.

Reference： [1] Patent: US2003/181719, 2003, A1

[ 186435-66-5 ] Synthesis Path-Downstream 1~6

1
[ 5414-19-7 ]
[ 186435-66-5 ]
[ 478920-99-9 ]

Yield	Reaction Conditions	Operation in experiment
		Example 4 Synthesis of 6-Amino-2-methoxy-3-[2-(2-bromoethoxy)ethyl]-4-pyrimidone Scheme 1 was used with 9.3 g of <strong>[186435-66-5]6-amino-2-methoxy-4-pyrimidone</strong> and 1.3 eq of bis(2-bromoethyl)ether, yielding 35% of the title compound. The O4 isomer was obtained in 20% yield.

Reference： [1]Patent: US2003/114414,2003,A1

2
4-bromo-1-butyronitrile [ No CAS ]
[ 186435-66-5 ]
[ 478920-82-0 ]

Yield	Reaction Conditions	Operation in experiment
65%	With lithium bromide; In chloroform; water; N,N-dimethyl-formamide;	Example 2 Synthesis of 6-Amino-2-methoxy-3-(3-cyanopropyl)-4-pyrimidone Sodium hydride (3.4 g of 60%, 85 mmol) was added to a mixture of <strong>[186435-66-5]6-amino-2-methoxy-4-pyrimidone</strong> (10.0 g, 71 mmol) in DMF at 0 C. Then lithium bromide (8.0 g, 92 mmol) was added, and the mixture was stirred for 1 hour at room temperature. The mixture was added dropwise to a solution of 4-bromo-1-butyronitrile (15.7 g, 106 mmol) in DMF at 80 C., and the reaction mixture was stirred at 80 C. for 8 hours. After cooling to room temperature, the solvent was removed in vacuo. Water was added and the mixture was extracted with chloroform, and the organic extracts were dried over sodium sulfate. After removal of chloroform, the residue was purified by chromatography on silica gel using chloroform:methanol as eluent. After separation of 6-amino-2-methoxy-4-(3-cyanopropoxy)pyrimidine (about 30%), 6-amino-2-methoxy-3-(3-cyanopropyl)-4-pyrimidone (9.73 g, 65%) was isolated as a white solid. 300 MHz 1H NMR (DMSO-d6): delta 1.78 (m, 2H, CH2), 2.50 (t, 2H, CH2CN) 3.84 (t, 2H, CH2N), 3.88 (s, 3H, CH3O), 4.83 (s, 1H, C5-H), 6.44 (s, 2H, NH2) ppm.
65%	With lithium bromide; In chloroform; water; N,N-dimethyl-formamide;	6-Amino-2-methoxy-3-(3-cyanopropyl)-4-pyrimidone Sodium hydride (1.2 eq) was added to a mixture of 6-amino-2-methoxypyrimidin-4-one (1 eq) in DMF at 0 C. Then lithium bromide (1.4 eq) was added, and the mixture was stirred for 1 hour at room temperature. The mixture was added dropwise to a solution of 4-bromo-1-butyronitrile (1.5 eq) in DMF at 80 C., and the reaction mixture was stirred at 80 C. for 5 hours. After cooling to room temperature, the solvent was removed in vacuo. Water was added and the mixture was extracted with chloroform, and the organic extracts were dried over sodium sulfate. After removal of chloroform, the residue was purified by chromatography on silica gel using chloroform:methanol as eluent to give 6-amino-2-methoxy-3-(3-cyanopropyl)pyrimidin-4(3H)-one (yield 65%) as a white solid. 300 MHz 1H NMR (DMSO-d6): delta 1.78 (m, 2H, CH2), 2.50 (t, 2H, CH2CN) 3.84 (t, 2H, CH2N), 3.88 (s, 3H, CH3O), 4.83 (s, 1H, C5-H), 6.44 (s, 2H, NH2) ppm.

Reference： [1]Patent: US2003/114414,2003,A1
[2]Patent: US2003/114445,2003,A1

3
[ 186435-66-5 ]
[ 4753-59-7 ]
[ 478920-93-3 ]

Yield	Reaction Conditions	Operation in experiment
54%	With lithium bromide; In N,N-dimethyl-formamide;	6-Amino-2-methoxy-3-(4-acetoxybutyl)pyrimidin-4(3H)-one Sodium hydride (1.2 eq) was added to the mixture of <strong>[186435-66-5]6-amino-2-methoxy-4-pyrimidone</strong> (1 eq) in DMF at 0 C. Then lithium bromide (1.5 eq) was added to the mixture and stirred for 1 hour at room temperature. The mixture was added dropwise to a solution of 4-bromo-1-acetoxybutane (1.5 eq) in DMF at 50 C. Workup and chromatography gave 6-amino-2-methoxy-3-(4-acetoxybutyl)-4-pyrimidone (yield 54%) as a white solid. 300 MHz 1H NMR (DMSO-d6): delta 1.52 (m, 4H, 2*CH2), 2.0 (s, 3H, CH3CO) 3.76 (t, 2H, CH2O), 3.88 (s, 3H, CH3N),), 4.0 (t, 2H, CH2O), 4.82 (s, 1H, C5-H), 6.41 (s, 2H, NH2)ppm.

Reference： [1]Patent: US2003/114445,2003,A1

4
[ 186435-66-5 ]
[ 54149-17-6 ]
[ 484682-45-3 ]

Yield	Reaction Conditions	Operation in experiment
42%	With N-benzyl-N,N,N-triethylammonium chloride; potassium carbonate; In acetone;	6-Amino-2-methoxy-3-[2-(2-methoxyethoxy)ethyl]-4-pyrimidone The mixture of <strong>[186435-66-5]6-amino-2-methoxy-4-pyrimidone</strong> (1 eq), potassium carbonate (1.5 eq), benzyltriethylammonium chloride (0.3 eq) and 2-(2-methoxyethoxy)ethyl bromide (1.5 eq) in acetone was heated at reflux overnight. After cooling to room temperature, the insoluble salts were filtered off and the solvent was removed. The residue was purified by chromatography on silica gel with chloroform:methanol (98:2-95:5) as eluent, to give 6-amino-2-methoxy-3-[2-(2-methoxyethoxy)ethyl]-4-pyrimidone (yield 42%) as a white solid. 300 MHz 1H NMR (DMSO-d6): delta 3.22 (s, 3H, CH3O), 3.38 (m, 2H, CH2O), 3.47 (m, 4H, 2*CH2), 3.85 (s, 3H, CH3O), 3.91 (t, 2H, CH2N), 4.81 (s, 1H, C5-H), 6.36 (s, 2H, NH2) ppm.

Reference： [1]Patent: US2003/114445,2003,A1

5
[ 186435-66-5 ]
CHCl₃/MeOH [ No CAS ]
[ 4753-59-7 ]
[ 479069-83-5 ]

Yield	Reaction Conditions	Operation in experiment
6.5 g (15%)	With lithium bromide; In N,N-dimethyl-formamide; mineral oil;	Method A. Sodium hydride (60% dispersion in mineral oil, 8.2 g, 205 mmol) was added to a mixture of <strong>[186435-66-5]6-amino-2-methoxy-4-pyrimidone</strong> (24.0 g, 170 mmol) in DMF at 0 C. After 0.5 hours, lithium bromide (19.2 g, 221 mmol) was added to the mixture and stirred for 0.5 hours at room temperature. The temperature was slowly increased to 70 C., and a solution of 4-bromobutyl acetate (50 g, 256 mmol) in DMF was added dropwise to the reaction mixture. The mixture was stirred at 70 C. for 3 hours. After cooling to room temperature, the solvent was removed in vacuo. The residue was purified by chromatography on silica gel using CHCl3/MeOH (1-5%) as eluent to give first 6.5 g (15%) of 6-amino-2-methoxy-4-(4-acetoxybutyl)pyrimidine as a white solid followed by 23.4 g (yield 54%) of 6-amino-2-methoxy-3-(4-acetoxybutyl)-4-pyrimidone as a white solid.

Reference： [1]Patent: US2003/181719,2003,A1

6
[ 186435-66-5 ]
[ 4753-59-7 ]
[ 478920-93-3 ]
[ 479069-83-5 ]

Yield	Reaction Conditions	Operation in experiment
34.5%	With potassium carbonate; In acetone;	Alternative Method B. A mixture of <strong>[186435-66-5]6-amino-2-methoxy-4-pyrimidone</strong> (30 g, 212.6 mmol), K2CO3 (44 g, 318 mmol), benzyltriethylammionium chloride (20 g, 88 mmol) and 4-bromobutyl acetate (60 g, 308 mmol) in acetone (800 ml) was heated at reflux overnight. After cooling to room temperature, the insoluble salts were filtered off and the solvent was removed. The residue was purified by chromatography on silica gel with CHCl3/MeOH (100:2-100:5) as eluent. After separation of 6-amino-2-methoxy-4-(4-acetoxybutyl)pyrimidine (22.8, yield 42%), 18.7 g (yield 34.5%) of 6-amino-2-methoxy-3-(4-acetoxybutyl)-4-pyrimidone was isolated as a white solid.

Reference： [1]Patent: US2003/181719,2003,A1

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Physical hazards
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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
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H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
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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
H250	Catches fire spontaneously if exposed to air
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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
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H290	May be corrosive to metals
Health hazards
Code	Phrase
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H301	Toxic if swallowed
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H316	Causes mild skin irritation
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H318	Causes serious eye damage
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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. 186435-66-5 ]

Quality Control of [ 186435-66-5 ]

Related Doc. of [ 186435-66-5 ]

Product Details of [ 186435-66-5 ]

Computed Properties of [ 186435-66-5 ]

Safety of [ 186435-66-5 ]

Application In Synthesis of [ 186435-66-5 ]

[ 186435-66-5 ] Synthesis Path-Upstream 1~1

[ 186435-66-5 ] Synthesis Path-Downstream 1~6

Related Functional Groups of [ 186435-66-5 ]

Amines

Alcohols

Ethers

Related Parent Nucleus of [ 186435-66-5 ]

Pyrimidines

Precautionary Statements-General

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[ 186435-66-5 ]

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[ 186435-66-5 ]