N-[4-[2-(2,4-dimethylphenoxy)phenyl]-1,3-thiazol-2-yl]-1,4,5,6-tetrahydropyrimidin-2-amine Chemical Properties

Melting point:

199 °C

storage temp. 

under inert gas (nitrogen or Argon) at 2–8 °C

solubility 

DMF: 10 mg/mL; DMSO: 2.5 mg/mL; Ethanol: 0.3 mg/mL; PBS (pH 7.2): 0.3 mg/mL

form 

powder to crystal

color 

White to Light yellow

InChI

InChI=1S/C21H22N4OS/c1-14-8-9-18(15(2)12-14)26-19-7-4-3-6-16(19)17-13-27-21(24-17)25-20-22-10-5-11-23-20/h3-4,6-9,12-13H,5,10-11H2,1-2H3,(H2,22,23,24,25)

InChIKey

TYBHXIFFPVFXQW-UHFFFAOYSA-N

SMILES

C1(NC2=NC(C3=CC=CC=C3OC3=CC=C(C)C=C3C)=CS2)NCCCN=1

Safety Information

HS Code 

2934.10.2000

N-[4-[2-(2,4-dimethylphenoxy)phenyl]-1,3-thiazol-2-yl]-1,4,5,6-tetrahydropyrimidin-2-amine Usage And Synthesis

Originator

Abafungin,York Pharma

Uses

Abafungin is a broad-spectrum antifungal agent.

Definition

ChEBI: A member of the class of guanidines that is tetrahydropyrimidin-2(1H)-imine in which the hydrogen of the imino group is replaced by a thiazol-2-yl group which in turn is substituted by a 2-(2,4-dimethylphenoxy)phenyl group at position 4 It has been used for the topical treatment of fungal nail infections.

Manufacturing Process

15.8 g (0.12 mole) N-(1,4,5,6-tetrahydropyrimidinyl)thiourea were added to 27.45 g (0.1 mole) 2-(2,4-dimethylphenoxy)phenacyl chloride in 100 ml acetone and heated to reflux for 2 hours. On cooling the falling out product was filtered off, washed with acetone and dried. N-[4-[2-(2,4- Dimethylphenoxy)phenyl]-2-thiazolyl]-1,4,5,6-tetrahydro-2-pyrimidinamine hydrochloride was prepared. Yield 91.4%; MP: 160°C.
20.72 g (0.05 mole) above product was stirred with 300 ml 1 N sodium hydroxide for 30 minutes at room temperature. The insoluble product was filtered off, washed and dried. Yield of N-[4-[2-(2,4-dimethylphenoxy)phenyl]- 2-thiazolyl]-1,4,5,6-tetrahydro-2-pyrimidinamine was 16.2 g (86%). MP: 191°-192°C.

Therapeutic Function

Antibacterial, Antifungal

N-[4-[2-(2,4-dimethylphenoxy)phenyl]-1,3-thiazol-2-yl]-1,4,5,6-tetrahydropyrimidin-2-amine(129639-79-8)Related Product Information

• N-[4-[2-(2,4-dimethylphenoxy)phenyl]-1,3-thiazol-2-yl]-1,4,5,6-tetrahydropyrimidin-2-amine
• 2-(2-Amino-thiazol-4-yl)-phenol
• 4-(2-METHOXY-PHENYL)-THIAZOL-2-YLAMINE