2-Amino-4-methoxypyrimidine NEW

2-Amino-4-methoxypyrimidine (CAS No.: 155-90-8) – Technological Innovations and Market Opportunities for Pyrimidine Drug Intermediates

I. Basic Information and Physicochemical Properties

Chinese Name: 2-Amino-4-methoxypyrimidine
English Name: 2-Amino-4-methoxypyrimidine
CAS No.: 155-90-8
Molecular Formula: C₅H₇N₃O
Molecular Weight: 125.13
Appearance: White to light yellow crystalline powder
Melting Point: 150-152℃
Boiling Point: 328℃ (atmospheric pressure)
Density: 1.26 g/cm³
Solubility: Slightly soluble in water (0.5g/100mL, 25℃), easily soluble in methanol, ethanol, DMF, and other polar solvents.

Chemical Properties:

• Basicity: The amino group (-NH₂) confers weak basicity (pKa≈9.8), allowing salt formation with acids.

• Reactivity: The methoxy group (-OCH₃) at the 4-position undergoes nucleophilic substitution reactions, reacting with reagents such as halogenated hydrocarbons and amines to form derivatives.

• Stability: Stable to acids, but prone to hydrolysis and demethoxylation under strong alkaline conditions.

II. Upstream and Downstream Industry Chain Analysis

Upstream Raw Materials and Synthesis Process

Core Raw Materials:

• 4-Methoxypyrimidine-2-one (CAS: 5245-59-2)

• Ammonia water (NH₃·H₂O)

Synthesis Route:

1. Step 1: 4-Methoxypyrimidine-2-one reacts with excess ammonia water in a high-pressure reactor at 150-180℃ and 3-5 MPa for 12-16 hours.

2. Step 2: After cooling and crystallization, the product is filtered and recrystallized from ethanol to obtain a purity ≥99% with a yield of 78-82%.

Downstream Products and Derivatives

Pharmaceutical Field:

• Antimalarial Drugs: Reacts with haloalkanes to form 2-alkylamino-4-methoxypyrimidine, a precursor for synthesizing mefloquine.

• Anticancer Drugs: Serves as an intermediate for tyrosine kinase inhibitors, used in synthesizing EGFR-targeted drugs (e.g., a key intermediate for osimertinib).

Agrochemical Field:

• Herbicides: Condenses with triazine compounds to form pyrimidine-oxybenzoic acid herbicides (e.g., pyriminoether), effective against annual grass weeds.

• Fungicides: Synthesized via oximination reactions to produce pyrimidine oxime fungicides, showing significant efficacy against wheat rust.

Materials Science:

• Organic Semiconductors: Copolymerizes with thiophene to prepare conjugated polymers for organic field-effect transistors (OFETs).

• Fluorescent Materials: Modified with fluorescent groups to prepare biological probes for live-cell imaging.

III. Analysis of Core Application Areas

1. Pharmaceutical R&D

• Antimalarial Drug Innovation:
  2-Amino-4-methoxypyrimidine condenses with 1,3-dichloroacetone to form a key intermediate for mefloquine, which has 5 times the antimalarial activity of traditional drug quinine and low drug resistance.

• Antiviral Drugs:
  Acts as a nucleoside analog precursor for synthesizing anti-influenza drugs (e.g., favipiravir intermediates), inhibiting RNA polymerase activity.

2. Agrochemical Creation

• Selective Herbicides:
  Reacts with 2,4-dichlorophenoxyacetic acid ethyl ester to form pyrimidine-oxyphenoxypropionic acid herbicides, achieving over 95% control efficacy against barnyard grass in rice fields.

• Novel Fungicides:
  Introduces methoxy groups to synthesize pyrimidine methoxyacrylate fungicides, providing 91% control efficacy against cucumber powdery mildew with a duration of over 15 days.

3. Advanced Materials

• Organic Optoelectronic Materials:
  Copolymerizes with fluorene compounds to prepare blue-emitting materials, with OLED devices achieving an external quantum efficiency (EQE) of 25% and a lifetime exceeding 10,000 hours.

• Lithium-ion Batteries:
  Used as an electrolyte additive to form a stable SEI film on the electrode surface, enhancing battery cycle life to over 2000 cycles.

IV. Technological Advantages and Market Dynamics

Technological Barriers:

• The amination reaction requires high-pressure conditions. Adopting continuous flow microreaction technology shortens the reaction time to 6 hours and reduces energy consumption by 40%.

Capacity Distribution:

• Global annual production capacity is approximately 200 tons, with China accounting for 65%. Major manufacturers include Zhejiang Hisoar Pharmaceutical and Jiangsu Lianhua Technology.

Market Demand:

• Driven by demand for antimalarial drugs and novel agrochemicals, the demand for this intermediate increased by 22% year-on-year in 2024, and the market size is expected to exceed 50 million yuan in 2025.

V. Safety and Storage Recommendations

Hazards:

• Mildly irritating to the skin. Wear protective gloves and goggles during handling.

Storage Conditions:

• Store in a sealed container in a cool, dry place (≤25℃), protected from light and moisture, and away from strong acids and bases.

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