3977-29-5

Basic information

• Product Name: 2-Amino-6-methyl-4-pyrimidinol
• Synonyms: 1n-22636;2-Amino-4-hydroxy-4-methylpyrimidine;2-amino-6-methyl-4(1h)-pyrimidinon;2-amino-6-methyl-4(1h)-pyrimidinone;2-amino-6-methyl-4-pyrimidino;4(1H)-Pyrimidinone, 2-amino-6-methyl-;4-Methylisocytosine;Mecytosine
• CAS NO: 3977-29-5
• Molecular Formula: C₅H₇N₃O
• Molecular Weight: 125.13
• EINECS: 223-612-1
• Product Categories: PYRIMIDINE;Fluorobenzene;Amines;Pyrimidines;Heterocycle-Pyrimidine series
• Mol File: 3977-29-5.mol
• Article Data: 25

Chemical Properties

• Melting Point: >300 °C(lit.)
• Boiling Point: 232.57°C (rough estimate)
• Flash Point: 107.1 °C
• Appearance: White to cream/Powder
• Density: 1.2602 (rough estimate)
• Vapor Pressure: 0.0183mmHg at 25°C
• Refractive Index: 1.6190 (estimate)
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• PKA: 10.03±0.50(Predicted)
• BRN: 3531
• CAS DataBase Reference: 2-Amino-6-methyl-4-pyrimidinol(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Amino-6-methyl-4-pyrimidinol(3977-29-5)
• EPA Substance Registry System: 2-Amino-6-methyl-4-pyrimidinol(3977-29-5)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 24/25-36/37/39-26-22
• WGK Germany: 3
• RTECS: UW7362250
• HazardClass: IRRITANT
• Hazardous Substances Data: 3977-29-5(Hazardous Substances Data)

Usage

Chemical Properties

white powder

Definition

ChEBI: An aminopyrimidine compound having its amino group at position 2 and hydroxy and methyl substituents at positions 4 and 6 respectively.

InChI:InChI=1/C5H7N3O/c1-3-2-4(9)8-5(6)7-3/h2H,1H3,(H3,6,7,8,9)

Synthetic route

→ 2-amino-6-methylpyrimidin-4-ol

3-methoxy-but-2-enoic acid ethyl ester (3510-99-4) + guanidine hydrochloride (50-01-1) → 2-amino-6-methylpyrimidin-4-ol (3977-29-5)

Conditions	Yield
In methanol at 100℃; for 3h; Solvent;	62.1%

+ guanidine nitrate (113-00-8) → 2-amino-6-methylpyrimidin-4-ol (3977-29-5)

Conditions	Yield
In ethanol; acetone at 20℃; for 10h;	52%

diguanidine carbonate (593-85-1) + ethyl acetoacetate (141-97-9) → 2-amino-6-methylpyrimidin-4-ol (3977-29-5)

Conditions	Yield
In ethanol Heating;

guanidine hydrochloride (50-01-1) + acetoacetic acid methyl ester (105-45-3) → 2-amino-6-methylpyrimidin-4-ol (3977-29-5)

Conditions	Yield
With potassium tert-butylate In methanol at 23 - 60℃;

guanidine nitrate (506-93-4) + ethyl acetoacetate (141-97-9) → 2-amino-6-methylpyrimidin-4-ol (3977-29-5)

Conditions	Yield
With potassium n-butoxide In butan-1-ol

2-amino-6-methylpyrimidin-4-ol (3977-29-5) → 2-amino-6-methyl-4-chloropyrimidine (5600-21-5)

Conditions	Yield
With trichlorophosphate for 2h; Reflux;	98%
With trichlorophosphate Heating;
With tetraethylammonium chloride; N,N-dimethyl-aniline; trichlorophosphate In acetonitrile at 110℃; for 0.333333h;

2-amino-6-methylpyrimidin-4-ol (3977-29-5) + 1,1'-carbonyldiimidazole (530-62-1) → N-(4-methyl-6-oxo-1,6-dihydropyrimidin-2-yl)-1H-imidazole-1-carboxamide (561316-60-7)

Conditions	Yield
In dimethyl sulfoxide at 80℃; for 1h;	98%

2-amino-6-methylpyrimidin-4-ol (3977-29-5) + Hexamethylene diisocyanate (822-06-0) → 2-(6-isocyanato-hexylaminocarbonylamino)-6-methyl-4(1H)-pyrimidinone (320393-85-9)

Conditions	Yield
at 100℃; for 16h;	98%
at 100℃; for 12h; Inert atmosphere;	90%

1-isocyanatooctane (3158-26-7) + 2-amino-6-methylpyrimidin-4-ol (3977-29-5) → 1-(6-methyl-4-oxo-1,4-dihydropyrimidin-2-yl)-3-octylurea

Conditions	Yield
In tetrahydrofuran for 48h; Heating;	97%
	97%

2-amino-6-methylpyrimidin-4-ol (3977-29-5) + Hexamethylene diisocyanate (822-06-0) → 2-(6-isocyanatohexylaminocarbonylamino)-6-methyl-4-pyrimidinone (320393-85-9)

Conditions	Yield
With pyridine at 100℃; Inert atmosphere;	95%
at 95℃; for 18h; Inert atmosphere;	94%
With pyridine In pentane at 100℃; Inert atmosphere;	90%

2-amino-6-methylpyrimidin-4-ol (3977-29-5) + 5-(4-Nitro-phenyl)-furan-2-carbonyl isothiocyanate (140160-21-0) → 1-(4-hydroxy-6-methyl-pyrimidin-2-yl)-3-[5-(4-nitro-phenyl)-furan-2-carbonyl]-thiourea (847981-73-1)

Conditions	Yield
With PEG-400 In acetonitrile ultrasonic irradiation;	86%

α-bromoacetophenone (70-11-1) + 2-amino-6-methylpyrimidin-4-ol (3977-29-5) → 5-hydroxy-7-methyl-2-phenylimidazo[1,2-a]pyrimidine (95980-02-2)

Conditions	Yield
In N,N-dimethyl-formamide for 4h; Reflux; Inert atmosphere;	85%
In N,N-dimethyl-formamide for 3h; Heating;	80%

2-amino-6-methylpyrimidin-4-ol (3977-29-5) + benzoic acid (65-85-0) → 2-benzamido-6-methylisocytosine (54286-79-2)

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In chloroform	85%

2-amino-6-methylpyrimidin-4-ol (3977-29-5) → 2-amino-4-hydroxy-6-methyl-5-nitropyrimidine (4214-85-1)

Conditions	Yield
With sulfuric acid; nitric acid for 0.75h; Ambient temperature;	83%

2-amino-6-methylpyrimidin-4-ol (3977-29-5) + 4-(1,1-dimethylethyl)benzoic acid (98-73-7) → 2-(4'-tert-butyl)benzamido-6-methylisocytosine (1260495-73-5)

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In chloroform for 16h; Inert atmosphere; Reflux;	83%

Hexyl isocyanate (2525-62-4) + 2-amino-6-methylpyrimidin-4-ol (3977-29-5) → N-hexyl-N'-(6-methyl-4-oxo-1,4-dihydropyrimidin-2-yl)urea

Conditions	Yield
With pyridine for 16h; Heating;	82%

6-Hydroxy-2-naphthoic acid (16712-64-4) + 2-amino-6-methylpyrimidin-4-ol (3977-29-5) → C11H8O3*2C5H7N3O

Conditions	Yield
In ethanol; water for 240h;	82%

4-nitrobenzenediazonium chloride (100-05-0) + 2-amino-6-methylpyrimidin-4-ol (3977-29-5) → 2-Amino-6-methyl-5-(4-nitro-phenylazo)-pyrimidin-4-ol

Conditions	Yield
	81%

3-nitrophenyldiazonium chloride (2028-76-4) + 2-amino-6-methylpyrimidin-4-ol (3977-29-5) → 2-Amino-6-methyl-5-(3-nitro-phenylazo)-pyrimidin-4-ol

Conditions	Yield
	81%

p-chlorobenzenediazonium chloride (2028-74-2) + 2-amino-6-methylpyrimidin-4-ol (3977-29-5) → 2-Amino-5-(4-chloro-phenylazo)-6-methyl-pyrimidin-4-ol

Conditions	Yield
	80%

2-nitrobenzenediazonium chloride (119-66-4) + 2-amino-6-methylpyrimidin-4-ol (3977-29-5) → 2-Amino-6-methyl-5-(2-nitro-phenylazo)-pyrimidin-4-ol

Conditions	Yield
	80%

2-chlorobenzenediazonium chloride (89-90-7) + 2-amino-6-methylpyrimidin-4-ol (3977-29-5) → 2-Amino-5-(2-chloro-phenylazo)-6-methyl-pyrimidin-4-ol

Conditions	Yield
	78%

2-amino-6-methylpyrimidin-4-ol (3977-29-5) + Glycine ethyl ester isocyanate (2949-22-6) → [3-(6-methyl-4-oxo-1,4-dihydropyrimidin-2-yl)ureido]acetic acid ethyl ester (583040-82-8)

Conditions	Yield
With pyridine for 3h; Heating;	78%

2-amino-6-methylpyrimidin-4-ol (3977-29-5) + 5-(2-chlorophenyl)-2-furoylisothiocyanate (304437-60-3) → 1-[5-(2-chloro-phenyl)-furan-2-carbonyl]-3-(4-hydroxy-6-methyl-pyrimidin-2-yl)-thiourea

Conditions	Yield
With PEG-400 In acetonitrile ultrasonic irradiation;	77%

2-bromo benzene diazonium chloride (34835-57-9) + 2-amino-6-methylpyrimidin-4-ol (3977-29-5) → 2-Amino-5-(2-bromo-phenylazo)-6-methyl-pyrimidin-4-ol

Conditions	Yield
	76%

2-amino-6-methylpyrimidin-4-ol (3977-29-5) + 2,3'-dibromoacetophenone (18523-22-3) → 2-(3-bromophenyl)-7-methylimidazo[1,2-a]pyrimidin-5-ol

Conditions	Yield
In N,N-dimethyl-formamide for 4h; Reflux; Inert atmosphere;	76%

benzene diazonium chloride (100-34-5) + 2-amino-6-methylpyrimidin-4-ol (3977-29-5) → 2-amino-4-hydroxy-6-methyl-5-phenylazopyrimidine

Conditions	Yield
	75%

(4-bromophenyl)diazonium chloride (2028-85-5) + 2-amino-6-methylpyrimidin-4-ol (3977-29-5) → 2-Amino-5-(4-bromo-phenylazo)-6-methyl-pyrimidin-4-ol

Conditions	Yield
	74%

2,3,5,6-tetrafluoroterephthalic acid (652-36-8) + water (7732-18-5) + 2-amino-6-methylpyrimidin-4-ol (3977-29-5) → C5H8N3O(1+)*0.5C8F4O4(2-)*0.5C8H2F4O4*H2O

Conditions	Yield
In 1,4-dioxane	74%

3-methoxy-benzenediazonium; chloride (19183-05-2) + 2-amino-6-methylpyrimidin-4-ol (3977-29-5) → 2-Amino-5-(3-methoxy-phenylazo)-6-methyl-pyrimidin-4-ol

Conditions	Yield
	72%

N-4-N,N-dimethylaminophenylmethylene-2-methyl-5-4H-oxazoline (1787-23-1) + 2-amino-6-methylpyrimidin-4-ol (3977-29-5) → 1-(4-chloro-6-methylpyrimidin-2-yl)-4-(4-(dimethylamino)benzylidene)-2-methyl-1H-imidazol-5(4H)-one (1575728-38-9)

Conditions	Yield
With potassium acetate; acetic acid Heating;	71%

para-methoxyphenyldiazonium chloride (4346-59-2) + 2-amino-6-methylpyrimidin-4-ol (3977-29-5) → 2-Amino-5-(4-methoxy-phenylazo)-6-methyl-pyrimidin-4-ol

Conditions	Yield
	70%

iodotrifluoromethane (2314-97-8) + 2-amino-6-methylpyrimidin-4-ol (3977-29-5) → 2-amino-5-trifluoromethyl-4-hydroxy-6-methylpyrimidine (1063697-18-6)

Conditions	Yield
With dihydrogen peroxide; iron(II) sulfate In water; dimethyl sulfoxide	70%

2-methyl-4-(4-chlorobenzylidene)-4H-oxazol-5-one (93634-55-0, 3237-71-6) + 2-amino-6-methylpyrimidin-4-ol (3977-29-5) → 4-(4-chlorobenzylidene)-1-(4-hydroxy-6-methylpyrimidin-2-yl)-2-phenyl-1H-imidazol-5(4H)-one (1575727-87-5)

Conditions	Yield
With potassium acetate; acetic acid Heating;	69%

Upstream product

• 29214-62-8 3-acetoxy-crotonic acid ethyl ester 
• 593-85-1 diguanidine carbonate 
• 603-69-0 ethyl 2-acetylacetoacetate 
• 141-97-9 ethyl acetoacetate 
• 113-00-8 guanidine nitrate 
• 50-01-1 guanidine hydrochloride 
• 124-46-9 guanidine hydrogen carbonate 
• 3510-99-4 3-methoxy-but-2-enoic acid ethyl ester 
• 5424-21-5 2,4-dichloro-6-methylpyrimidine 
• 6307-35-3 2-amino-5-bromo-6-methylpyrimidin-4(3H)-one 
• 98-80-6 phenylboronic acid 
• 105-45-3 acetoacetic acid methyl ester 
• 13509-52-9 1,3,6-trimethyluracil 
• 55996-28-6 6-methyl-2-methoxy-4(3H)-pyrimidinone 

Downstream Products

• 5600-21-5 2-amino-6-methyl-4-chloropyrimidine 
• 847981-73-1 1-(4-hydroxy-6-methyl-pyrimidin-2-yl)-3-[5-(4-nitro-phenyl)-furan-2-carbonyl]-thiourea 
• 1136979-77-5 C₂₀H₁₇N₅O₃ 
• 70483-81-7 2-amino-4-benzyloxy-6-methylpyrimidine 
• 1374830-72-4 C₁₈H₁₄F₃N₅O₃S 
• 6951-49-1 2-amino-6-phenethylpyrimidin-4(3H)-one 
• 1620784-70-4 C₁₂H₁₁FN₄O₂ 
• 1620784-72-6 C₁₂H₁₁FN₄O₂ 

Relevant articles and documents

Synthesis and Plant Growth Stimulating Action of 2-Amino-6-methylpyrimidine-4(3H)-thione Derivatives

Abstract: A series of new pyrimidine derivatives, including those containing an azole or azine heterocycle linked through a sulfur atom or a thiomethylene group, was synthesized based on 2-amino-6-methylpyrimidine-4(3H)-thione. The synthesized compounds exhibited a pronounced stimulating effect on plants growth in the range of 43–96% compared to heteroauxin.

Regioselective synthesis of 6-substituted-2-amino-5-bromo-4(3H)- pyrimidinones and evaluation of their antiviral activity

A series of 2-amino-5-bromo-4(3 H)-pyrimidinone derivatives bearing different substituents at the C-6 position were synthesized using a highly regioselective lithiation-substitution protocol, and the effect of structural variation at the C-6 position on their antiviral activity in cell culture was evaluated. Although some of the derivatives were found to be active against various virus strains, they were effective only close to their toxicity threshold.

Theoretical investigation on the reactivity and photophysical properties of cobalt(II) and manganese(II) complexes constructed using Schiff base ligands based on ALIE and TDDFT calculations

Herein, we describe the synthesis of two novel Schiff base ligands, 2-[(3-bromo-5-hydroxybenzylidene)-amino]-6-methylpyrimidin-4-ol (1) and 3-bromo-5-[(5-methylthiazol-2-ylimino)methyl]phenol (2), and their Co(II) and Mn(II) complexes (4–6). The molecular

Synthesis and Investigation of Phthalazinones as Antitubercular Agents

A series of 2- and 7-substituted phthalazinones was synthesised and their potential as anti-tubercular drugs assessed via Mycobacterium tuberculosis (mc26230) growth inhibition assays. All phthalazinones tested showed growth inhibitory activity (MIC 100 μm), and those compounds containing lipophilic and electron-withdrawing groups generally exhibited better anti-tubercular activity. Several lead compounds were identified, including 7-((2-amino-6-(4-fluorophenyl)pyrimidin-4-yl)amino)-2-heptylphthalazin-1(2H)-one (MIC=1.6 μm), 4-tertbutylphthalazin-2(1H)-one (MIC=3 μm), and 7-nitro-phthalazin-1(2H)-one (MIC=3 μm). Mode of action studies indicated that selected pyrimidinyl-phthalazinones may interfere with NADH oxidation, however, the mode of action of the lead compound is independent of this enzyme. MIC=minimum inhibitory concentration.