Name: 2-Amino-4-chloro-6-methoxypyrimidine
SKU: 5734-64-5

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Basic Information

Molecular Structure:
CAS No.:	5734-64-5
Name:	2-Amino-4-chloro-6-methoxypyrimidine
Article Data:	22

Formula:	C₅H₆ClN₃O
Molecular Weight:	159.575
Synonyms:	2-Amino-4-methoxy-6-chloro-pyrimidine;2-Amino-4-methoxy-6-chloro pyrimidine;Pyrimidine, 2-amino-4-chloro-6-methoxy-;2-Pyrimidinamine, 4-chloro-6-methoxy-;2-Amino-4-methoxy-6-chloropyrimidine;4-Chloro-6-methoxy-pyrimidin-2-amine;
EINECS:	410-050-9
Density:	1.398 g/cm³
Melting Point:	168-171 °C(lit.)
Boiling Point:	349.357 °C at 760 mmHg
Flash Point:	165.086 °C
Appearance:	light yellow crystalline powder
Hazard Symbols:	Xn
Risk Codes:	22
Safety:	22-2

Synthetic route

: 67-56-1
methanol

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

: 124-41-4
sodium methylate

: 5734-64-5
2-amino-4-chloro-6-methoxypyrimidine

Conditions

Conditions	Yield
at 17℃; for 4.5h; Product distribution / selectivity; Heating / reflux;	97%
for 20h; Heating / reflux;	90%

...Expand

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

: 124-41-4
sodium methylate

: 5734-64-5
2-amino-4-chloro-6-methoxypyrimidine

Conditions

Conditions	Yield
In acetone at 17 - 30℃; for 6.5h; Product distribution / selectivity;	95.3%
In acetic acid methyl ester at 17 - 30℃; for 6.5h; Product distribution / selectivity;	94.6%
In methanol for 20h; Heating / reflux;	90%

: 67-56-1
methanol

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

: 5734-64-5
2-amino-4-chloro-6-methoxypyrimidine

Conditions

Conditions	Yield
With potassium carbonate at 20℃; for 2h; Product distribution / selectivity; Heating / reflux;	95%
With sodium methylate In methanol for 20h; Reflux;	90%
Stage #1: methanol With sodium hydride In tetrahydrofuran for 0.25h; Inert atmosphere; Stage #2: 2-Amino-4,6-dichloropyrimidine In tetrahydrofuran for 15h; Inert atmosphere;	84%

: 43212-41-5
2,4-dichloro-6-methoxypyrimidine

: 5734-64-5
2-amino-4-chloro-6-methoxypyrimidine

Conditions

Conditions	Yield
With ethanol; ammonia at 100℃;

2-amino-6-methoxy-3H-pyrimidin-4-one: 2-amino-6-methoxy-3H-pyrimidin-4-one

: 5734-64-5
2-amino-4-chloro-6-methoxypyrimidine

Conditions

Conditions	Yield
With trichlorophosphate

: 43212-41-5
2,4-dichloro-6-methoxypyrimidine

: 7664-41-7
ammonia

: 5734-64-5
2-amino-4-chloro-6-methoxypyrimidine

Conditions

Conditions	Yield
at 100℃; im Rohr;

: 90982-32-4
chlorimuron ethyl

A: 155-90-8
4-methoxypyrimidin-2-amine

B: 5734-64-5
2-amino-4-chloro-6-methoxypyrimidine

C: 59777-72-9
ethyl 2-(aminosulfonyl)benzoate

D: 81-07-2
saccharin

E: N-(6-Chloro-4-methoxypyrimidin-2-yl)urea

F: chlorimuron

G benzoic acid, ethyl benzoate: benzoic acid, ethyl benzoate

Conditions

Conditions	Yield
With water for 2h; Product distribution; Rate constant; Irradiation; var. pH values;

...Expand

: 5734-64-5
2-amino-4-chloro-6-methoxypyrimidine

: 100-61-8
N-methylaniline

: 25706-78-9
2-amino-6-(N-methylanilino)pyrimidin-4(3H)-one

Conditions

Conditions	Yield
at 289.84 - 299.84℃; for 0.0666667h;	97%

: 5734-64-5
2-amino-4-chloro-6-methoxypyrimidine

: C14H9NO6S

: sodium ((4-chloro-6-methoxypyrimidin-2-yl)carbamoyl)((2-(phenoxycarbonyl)phenoxy)sulfonyl)amide

Conditions

Conditions	Yield
Stage #1: 2-amino-4-chloro-6-methoxypyrimidine; C14H9NO6S In acetonitrile at 20℃; for 24h; Stage #2: With sodium hydrogencarbonate	97%

: 5734-64-5
2-amino-4-chloro-6-methoxypyrimidine

: 155-90-8
4-methoxypyrimidin-2-amine

Conditions

Conditions	Yield
With hydrogen; N-ethyl-N,N-diisopropylamine; palladium 10% on activated carbon In ethanol; ethyl acetate for 14h;	94%
With hydrogen; N-ethyl-N,N-diisopropylamine; palladium 10% on activated carbon In ethanol; ethyl acetate for 14h;	90%
With hydrogen; N-ethyl-N,N-diisopropylamine; palladium 10% on activated carbon In ethanol; ethyl acetate for 14h;	90%

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Specification

The 2-Amino-4-chloro-6-methoxypyrimidine, with the CAS registry number 5734-64-5, is also known as 2-Pyrimidinamine, 4-chloro-6-methoxy-. It belongs to the product categories of Pyridines, Pyrimidines, Purines and Pteredines; Pyrimidine; Pyrimidines; Building Blocks; Halogenated Heterocycles; Heterocyclic Building Blocks; Pyrimidines Heterocyclic Building Blocks. Its EINECS registry number is 410-050-9. This chemical's molecular formula is C₅H₆ClN₃O and molecular weight is 159.57. What's more, both its IUPAC name and systematic name are the same which is called 4-Chloro-6-methoxypyrimidin-2-amine. It should be stored in a cool, dry and sealed place. This chemical can be used for intermediates of pharmaceutical and chemical, it is also uesd for synthesis of the pesticide chlorimuron-ethyl.

Physical properties about 2-Amino-4-chloro-6-methoxypyrimidine are: (1)ACD/LogP: 1.035; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.03; (4)ACD/LogD (pH 7.4): 1.04; (5)ACD/BCF (pH 5.5): 3.60; (6)ACD/BCF (pH 7.4): 3.60; (7)ACD/KOC (pH 5.5): 87.04; (8)ACD/KOC (pH 7.4): 87.05; (9)#H bond acceptors: 4; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 1; (12)Polar Surface Area: 61.03 Å²; (13)Index of Refraction: 1.585; (14)Molar Refractivity: 38.245 cm³; (15)Molar Volume: 114.114 cm³; (16)Polarizability: 15.162×10^-24cm³; (17)Surface Tension: 57.284 dyne/cm; (18)Density: 1.398 g/cm³; (19)Flash Point: 165.086 °C; (20)Enthalpy of Vaporization: 59.384 kJ/mol; (21)Boiling Point: 349.357 °C at 760 mmHg; (22)Vapour Pressure: 0 mmHg at 25 °C.

Uses of 2-Amino-4-chloro-6-methoxypyrimidine: it is used to produce other chemicals. For example, it can react with 2-cyano-3,3-bis-methylsulfanyl-acrylic acid ethyl ester to get 3-(4-chloro-6-methoxy-pyrimidin-2-ylamino)-2-cyano-3-methylsulfanyl-acrylic acid ethyl ester. This reaction needs reagent NaH and solvents N,N-dimethyl-acetamide, toluene at ambient temperature. The yield is 85 %.

2-Amino-4-chloro-6-methoxypyrimidine can react with 2-cyano-3,3-bis-methylsulfanyl-acrylic acid ethyl ester to get 3-(4-chloro-6-methoxy-pyrimidin-2-ylamino)-2-cyano-3-methylsulfanyl-acrylic acid ethyl ester.

When you are dealing with this chemical, you should be very careful. This chemical may cause damage to health and it is harmful if swallowed. You should keep out of the reach of children. And the gas can not be breathed.

You can still convert the following datas into molecular structure:
(1) SMILES: Clc1nc(nc(OC)c1)N
(2) InChI: InChI=1S/C5H6ClN3O/c1-10-4-2-3(6)8-5(7)9-4/h2H,1H3,(H2,7,8,9)
(3) InChIKey: VFEYBTFCBZMBAU-UHFFFAOYSA-N

The toxicity data is as follows:

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
rat	LDLo	oral	11gm/kg (11000mg/kg)	BEHAVIORAL: TREMOR GASTROINTESTINAL: CHANGES IN STRUCTURE OR FUNCTION OF SALIVARY GLANDS LUNGS, THORAX, OR RESPIRATION: DYSPNEA	National Technical Information Service. Vol. OTS0540491,