2-Amino-4,6-dihydroxypyrimidine supplier

Name
2-Amino-4,6-dihydroxypyrimidine
EINECS 200-256-5
CAS No. 56-09-7
Article Data17
CAS DataBase
Density 1.84 g/cm³
Solubility Insoluble in water, insoluble in common organic solvent, soluble in alkaline solution.
Melting Point >300 °C(lit.)
Formula C₄H₅N₃O₂
Boiling Point 540.1 °C at 760 mmHg
Molecular Weight 127.103
Flash Point 280.4 °C
Transport Information
Appearance slightly white powder
Safety 24/25-36-26
Risk Codes 20/21/22-36/37/38
Molecular Structure
Hazard Symbols Xn
Synonyms 2-amino-6-hydroxy-3H-pyrimidin-4-one;2-Amino-4,6-dioxypyrimidine;4(1H)-Pyrimidinone, 2-amino-6-hydroxy-;2-Amino-6-hydroxy-4(1H)-pyrimidinone;2-Amino-4,6-pyrimidinedione;2-Amino-6-hydroxy-1H-pyrimidin-4-one;4,6-Dihydroxy-2-aminopyrimidine;
PSA 92.26000
LogP 0.05120

Synthetic route

: 506-93-4
guanidine nitrate

: 105-53-3
diethyl malonate

: 56-09-7
2-aminopyrimidine-4,6-diol

Conditions

Conditions	Yield
Stage #1: guanidine nitrate With sodium methylate In ethanol at 5℃; for 0.5h; Stage #2: diethyl malonate In ethanol at 65℃; for 6h; Solvent; Temperature;	96.1%
Stage #1: guanidine nitrate; diethyl malonate With sodium ethanolate In ethanol at 100℃; for 1h; Stage #2: With acetic acid In water pH=5; Temperature;	83.4%

: 124-46-9, 20734-13-8, 100224-74-6, 593-85-1
guanidine hydrogen carbonate

: 105-53-3
diethyl malonate

: 56-09-7
2-aminopyrimidine-4,6-diol

Conditions

Conditions	Yield
In ethanol for 60h; Reflux;	93%

: 50-01-1
guanidine hydrochloride

: 108-59-8
malonic acid dimethyl ester

: 56-09-7
2-aminopyrimidine-4,6-diol

Conditions

Conditions	Yield
With sodium methylate In methanol Reflux;	85%

: 50-01-1
guanidine hydrochloride

: 105-53-3
diethyl malonate

: 56-09-7
2-aminopyrimidine-4,6-diol

Conditions

Conditions	Yield
With sodium methylate In methanol at 70 - 75℃; for 5h;	82%
With sodium In ethanol for 3h; Reflux;	79.3%
With sodium carbonate In water at 60℃; for 0.5h; Reagent/catalyst; Sonication;	55%
With sodium ethanolate In ethanol
Stage #1: guanidine hydrochloride With sodium methylate at 90℃; for 0.166667h; Stage #2: diethyl malonate In methanol for 0.666667h; Temperature;

: guanidine hydrochloride salt

: 105-53-3
diethyl malonate

: 56-09-7
2-aminopyrimidine-4,6-diol

Conditions

Conditions	Yield
With sodium methylate In methanol at 70℃; for 5h;	82%

: 79-17-4
aminoguanidine

: 13937-08-1
2-hydroxy-malonic acid diethyl ester

: 56-09-7
2-aminopyrimidine-4,6-diol

: 141-82-2
malonic acid

: 57-13-6
urea

A: 4425-67-6
2-aminopyrimidine-4,6-diol

B: 873-83-6
4-Amino-2,6-dihydroxypyrimidine

C: 67-52-7
BARBITURIC ACID

D: 56032-78-1
2,4,6-trioxo-hexahydro-pyrimidine-5-carboxylic acid amide

E: C5H6N4O3

F: 56-09-7
2-aminopyrimidine-4,6-diol

G: 2345-56-4
Malonamic acid

Conditions

Conditions	Yield
at 60 - 85℃; for 72h;

...Expand

: 56-09-7
2-aminopyrimidine-4,6-diol

: 97-02-9
2,4-Dinitroanilin

: 2-amino-5-((2,4-dinitrophenyl)diazenyl)pyrimidine-4,6-diol

Conditions

Conditions	Yield
Stage #1: 2,4-Dinitroanilin With hydrogenchloride; sodium nitrite In water at 0℃; for 0.5h; Stage #2: 2-aminopyrimidine-4,6-diol With sodium hydroxide In water	100%

: 56-09-7
2-aminopyrimidine-4,6-diol

: 56-05-3
2-Amino-4,6-dichloropyrimidine

Conditions

Conditions	Yield
With triethylamine; trichlorophosphate at 40 - 90℃; for 2h;	98.8%
With bis(trichloromethyl) carbonate In toluene at 70 - 75℃; for 6h; Reagent/catalyst; Temperature; Solvent;	92%
With thionyl chloride for 4h; Reagent/catalyst; Temperature; Reflux;	92.7%

: 555-16-8
4-nitrobenzaldehdye

: 56-09-7
2-aminopyrimidine-4,6-diol

: 5,5'-(4-nitrobenzylidene)bis(2-amino-4,6-dihydroxypyrimidine)

Conditions

Conditions	Yield
In dimethyl sulfoxide at 100 - 110℃; for 0.333333h;	98%

: (E)-1-fluoro-4-(2-nitroprop-1-en-1-yl)benzene

: 56-09-7
2-aminopyrimidine-4,6-diol

: 2-amino-5-(4-fluorophenyl)-6-methylfuro[2,3-d]pyrimidin-4-ol

Conditions

Conditions	Yield
In water at 90℃; for 2h; Green chemistry;	95%

: 37629-52-0
(E)-1-(4-chlorophenyl)-2-nitropropene

: 56-09-7
2-aminopyrimidine-4,6-diol

: 2-amino-5-(4-chlorophenyl)-6-methylfuro[2,3-d]pyrimidin-4-ol

Conditions

Conditions	Yield
In water at 90℃; for 2h; Green chemistry;	93%

: 705-60-2, 18315-84-9, 58321-79-2
1-phenyl-2-nitroprop-1-ene

: 56-09-7
2-aminopyrimidine-4,6-diol

: 2-amino-6-methyl-5-phenylfuro[2,3-d]pyrimidin-4-ol

Conditions

Conditions	Yield
In water at 90℃; for 2h; Solvent; Temperature; Green chemistry;	92%

: 1120-82-7
pyrazole-1-methanol

: 56-09-7
2-aminopyrimidine-4,6-diol

: 2-(((1H-pyrazol-1-yl)methyl)amino)pyrimidine-4,6-diol

Conditions

Conditions	Yield
In acetonitrile at 20℃; for 96h;	91.22%

: 131981-75-4
(E)-1-bromo-4-(2-nitroprop-1-en-1-yl)benzene

: 56-09-7
2-aminopyrimidine-4,6-diol

: 2-amino-5-(4-bromophenyl)-6-methylfuro[2,3-d]pyrimidin-4-ol

Conditions

Conditions	Yield
In water at 90℃; for 2h; Green chemistry;	90%

: 52287-53-3
1-nitro-4-[(1E)-2-nitro-1-propenyl]benzene

: 56-09-7
2-aminopyrimidine-4,6-diol

: 2-amino-6-methyl-5-(4-nitrophenyl)furo[2,3-d]pyrimidin-4-ol

Conditions

Conditions	Yield
In water at 90℃; for 2h; Green chemistry;	89%

: 134538-50-4
(E)-1-nitro-3-(2-nitro-propenyl)-benzene

: 56-09-7
2-aminopyrimidine-4,6-diol

: 2-amino-6-methyl-5-(3-nitrophenyl)furo[2,3-d]pyrimidin-4-ol

Conditions

Conditions	Yield
In water at 90℃; for 2h; Green chemistry;	88%

: 52287-58-8
(E)-2,4-dichloro-1-(2-nitroprop-1-en-1-yl)benzene

: 56-09-7
2-aminopyrimidine-4,6-diol

: 2-amino-5-(2,4-dichlorophenyl)-6-methylfuro[2,3-d]pyrimidin-4-ol

Conditions

Conditions	Yield
In water at 90℃; for 2h; Green chemistry;	87%

: 37629-51-9
1-methoxy-4-((E)-2-nitroprop-1-enyl)benzene

: 56-09-7
2-aminopyrimidine-4,6-diol

: 2-amino-5-(4-methoxyphenyl)-6-methylfuro[2,3-d]pyrimidin-4-ol

Conditions

Conditions	Yield
In water at 90℃; for 2h; Green chemistry;	87%

: 186581-53-3, 908094-01-9
diazomethane

: 56-09-7
2-aminopyrimidine-4,6-diol

: 36315-01-2
4,6-dimethoxy-2-aminopyrimidine

Conditions

Conditions	Yield
In methanol; diethyl ether at 20℃; for 24h;	86%
In methanol; diethyl ether at 20℃; for 24h;	86%

: 131981-73-2
(E)-1-(2-nitroprop-1-en-1-yl)naphthalene

: 56-09-7
2-aminopyrimidine-4,6-diol

: 2-amino-6-methyl-5-(naphthalen-1-yl)furo[2,3-d]pyrimidin-4-ol

Conditions

Conditions	Yield
In water at 90℃; for 2h; Green chemistry;	86%

: (Z)-(2-nitroprop-1-en-1-yl)benzene

: 56-09-7
2-aminopyrimidine-4,6-diol

: 2-amino-6-methyl-5-phenylfuro[2,3-d]pyrimidin-4-ol

Conditions

Conditions	Yield
In water at 90℃; for 2h; Green chemistry;	86%

: 37629-59-7
(E)-2-(2-nitroprop-1-en-1-yl)thiophene

: 56-09-7
2-aminopyrimidine-4,6-diol

: 2-amino-6-methyl-5-(thiophen-2-yl)furo[2,3-d]pyrimidin-4-ol

Conditions

Conditions	Yield
In water at 90℃; for 2h; Green chemistry;	85%

: 52287-56-6
(E)-1-methyl-4-(2-nitroprop-1-en-1-yl)benzene

: 56-09-7
2-aminopyrimidine-4,6-diol

: 2-amino-6-methyl-5-(p-tolyl)furo[2,3-d]pyrimidin-4-ol

Conditions

Conditions	Yield
In water at 90℃; for 2h; Green chemistry;	85%

: 68-12-2, 33513-42-7
N,N-dimethyl-formamide

: 56-09-7
2-aminopyrimidine-4,6-diol

: 5604-46-6
2-amino-4,6-dichloropyrimidine-5-carboxaldehyde

Conditions

Conditions	Yield
Stage #1: N,N-dimethyl-formamide With trichlorophosphate at 5 - 10℃; Stage #2: 2-aminopyrimidine-4,6-diol Cooling; Reflux; Stage #3: With water	84%
With trichlorophosphate at 5 - 100℃; for 5h;	80.8%
With trichlorophosphate at 5 - 100℃; for 5h;	80.8%

: 485-47-2
indan-1,2,3-trione hydrate

: 56-09-7
2-aminopyrimidine-4,6-diol

: 2-amino-4,4b,9b-trihydroxy-4b,9b-dihydro-5H-indeno[2',1':4,5]furo[2,3-d]pyrimidin-5-one

Conditions

Conditions	Yield
With acetic acid In water at 80℃; for 2h;	83%

: 49678-57-1
(1E)-1-chloro-4-(2-nitrobut-1-en-1-yl)benzene

: 56-09-7
2-aminopyrimidine-4,6-diol

: 2-amino-5-(4-chlorophenyl)-6-ethylfuro[2,3-d]pyrimidin-4-ol

Conditions

Conditions	Yield
In water at 90℃; for 2h; Green chemistry;	79%

: 56-09-7
2-aminopyrimidine-4,6-diol

: methyl (Z)-4-(2-chloro-2-nitrovinyl)benzoate

: 222295-27-4
methyl 4-(2-amino-4(3H)-5-oxofuro<2,3-d>pyrimidine-5-yl)benzoate

Conditions

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In ethanol; butanone for 3h; Heating;	78%

: 127143-28-6
(Z)-1-(2-chloro-2-nitrovinyl)-4-methoxybenzene

: 56-09-7
2-aminopyrimidine-4,6-diol

: 2-amino-5-(4-methoxyphenyl)furo<2,3-d>pyrimidin-4(3H)-one

Conditions

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In ethanol; butanone for 3h; Heating;	77%

: 56-09-7
2-aminopyrimidine-4,6-diol

: 613-45-6
2,4-Dimethoxybenzaldehyde

: 5,5'-(2,4-dimethoxybenzylidene)bis(2-amino-4,6-dihydroxypyrimidine)

Conditions

Conditions	Yield
In dimethyl sulfoxide at 100 - 110℃; for 2h;	75%

: 100-10-7
4-dimethylamino-benzaldehyde

: 56-09-7
2-aminopyrimidine-4,6-diol

: 5,5'-(4-dimethylaminobenzylidene)bis(2-amino-4,6-dihydroxypyrimidine)

Conditions

Conditions	Yield
In dimethyl sulfoxide at 100 - 110℃; for 8h;	73%

: 56-09-7
2-aminopyrimidine-4,6-diol

: 78225-77-1
2-nitrobenzoyl isothiocyanate

: 1189349-40-3
C12H9N5O5S

Conditions

Conditions	Yield
In dichloromethane at 20℃; for 3h;	71%

2-Amino-4,6-dihydroxypyrimidine Specification

The 2-Amino-4,6-dihydroxypyrimidine with the cas number 56-09-7. It is also called 2-Amino-4-hydroxy-1H-pyrimidin-6-one name by IUPAC. It belongs to the following product categories: (1)Pyrimidine; (2)Pyridines; (3)Pyrimidines; (4)Purines and Pteredines; (5)Nucleotides and Nucleosides; (6)5-FOA; (7)Bases & Related Reagents; (8)Nucleotides. 2-Amino-4,6-dihydroxypyrimidine seem like white amorphous powder. It is water- absorpted in moist atmosphere.

Properties of 2-Amino-4-chloro-6-methylpyrimidine are: (1)ACD/LogP: -1.23 ; (2)# of Rule of 5 Violations: 0 ; (3)ACD/LogD (pH 5.5): -2.02 ; (4)ACD/LogD (pH 7.4): -3.77 ; (5)ACD/BCF (pH 5.5): 1 ; (6)ACD/BCF (pH 7.4): 1 ; (7)ACD/KOC (pH 5.5): 1 ; (8)ACD/KOC (pH 7.4): 1 ; (9)#H bond acceptors: 5 ; (10)#H bond donors: 4 ; (11)#Freely Rotating Bonds: 1 ; (12)Polar Surface Area: 45.14 Å² ; (13)Index of Refraction: 1.752 ; (14)Molar Refractivity: 28.15 cm³ ; (15)Molar Volume: 68.9 cm³ ; (16)Polarizability: 11.16 ×10^-24cm³ ; (17)Surface Tension: 89.4 dyne/cm ; (18)Density: 1.84 g/cm³ ; (19)Flash Point: 280.4 °C ; (20)Enthalpy of Vaporization: 84.83 kJ/mol ; (21)Boiling Point: 540.1 °C at 760 mmHg ; (22)Vapour Pressure: 2.81E-12 mmHg at 25°C

Uses of 2-Amino-4-chloro-6-methylpyrimidine are: It can be used for a kind of important pharmaceutical intermediates, especially as an intermediate of Bensulfuron methyl and Pyrazosulfuron-ethyl. In addtion, it can be used as reactant in many reaction. For instance, it can react with diacetoxy-phenyl-l³-iodane for reaction to get 2-amino-5-phenyliodonio(1H,5H)pyrimidine-4,6-dione.

When you are using this chemical, please be cautious about it as the following: It is quite irritating to eyes, respiratory system and skin. When you are using this chemical, please wear suitable gloves and eye/face protection to avoid contact with skin and eyes. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. Besides, Do not breathe dust, because it is quite harmful by inhalation, in contact with skin and if swallowed.

You can still convert the following datas into molecular structure :
1.SMILES:O=C1/C=C(/O)\N=C(\N)N1
2.InChI:InChI=1/C4H5N3O2/c5-4-6-2(8)1-3(9)7-4/h1H,(H4,5,6,7,8,9)

Toxic information of 2-Amino-4-chloro-6-methylpyrimidine can be showed as follows:

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
rat	LC	inhalation	> 5200mg/m3/4H (5200mg/m³)		National Technical Information Service. Vol. OTS0556385,
rat	LD50	oral	> 11gm/kg (11000mg/kg)		National Technical Information Service. Vol. OTS0556385,

Product Name

2-Amino-4,6-dihydroxypyrimidine

Synthetic route

2-Amino-4,6-dihydroxypyrimidine Specification

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