4-Amino-2,6-dimethoxypyrimidine

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Cat Number

INT3289507

CAS Number

3289-50-7

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Product Detail Description Customer Q&A

CAS Number

3289-50-7

EINECS

221-946-2

Storage

2-8℃

Synonyms

2,6-dimethoxy-4-pyrimidinamin;4-Amino-4,6-dimethoxypyrimidine;4-Amino-2,6-dimethoxy

Molecular Formula

C6H9N3O2

Molecular Weight

155.15

Smiles

C1(OC)=NC(OC)=CC(N)=N1

Appearance

White powder

Melting Point

149-152℃

Boiling Point

340℃

Relative Density

1.2

pKa

3.35

General Description

4-Amino-2,6-dimethoxypyrimidine is a pyrimidine derivative bearing amino and methoxy substituents at the C-4 and C-2/C-6 positions, respectively. The symmetrical dimethoxy substitution at C-2 and C-6 creates a unique electronic environment on the pyrimidine ring, with both positions ortho to the nitrogen atoms being occupied by electron-donating methoxy groups. The C-4 amino group is the primary site of nucleophilic reactivity and further functionalization.

Mechanism of Action

4-Amino-2,6-dimethoxypyrimidine functions as a pyrimidine building block in heterocyclic synthesis. The C-4 amino group can be diazotized and converted to a variety of functional groups via Sandmeyer-type reactions. The methoxy groups can be cleaved under acidic conditions (to reveal hydroxyl groups) or undergo ipso substitution with nucleophiles. The 2,6-dimethoxy pattern is found in trimethoprim (an antibiotic DHFR inhibitor) and related diaminopyrimidine drugs.

Application

4-Amino-2,6-dimethoxypyrimidine is used as an intermediate in the synthesis of diaminopyrimidine pharmaceuticals including trimethoprim, pyrimethamine (antimalarial), and related antifolate agents. The 2,4-diaminopyrimidine scaffold is a privileged structure in DHFR (dihydrofolate reductase) inhibitor design. It is also used in the synthesis of fungicides, herbicides, and UV-absorbing materials.

What is the recommended storage condition for 4-Amino-2,6-dimethoxypyrimidine?

It should be stored at 2-8°C in a well-sealed container, protected from moisture and direct light, to maintain its chemical integrity throughout the shelf life.

Is a Certificate of Analysis (COA) available for 4-Amino-2,6-dimethoxypyrimidine?

Yes, a fully verified COA is issued for every batch and can be shared electronically. Additional documentation such as MSDS or impurity profiles may be requested separately.

What scale of supply is available for 4-Amino-2,6-dimethoxypyrimidine for pilot or commercial synthesis?

Supply is available from laboratory research scale through multi-kilogram pilot quantities. Commercial-scale supply can be discussed based on projected demand.

What is the primary synthetic application of 4-Amino-2,6-dimethoxypyrimidine?

It is widely used as a key building block or intermediate in multi-step pharmaceutical synthesis workflows, providing versatile reactivity for constructing target molecular architectures.

What quantities of 4-Amino-2,6-dimethoxypyrimidine are available for order?

We accommodate orders of varying scale, from small research quantities through bulk commercial supply. Contact our sales team to discuss pack sizes and volume pricing.