668-44-0

Basic information

• Product Name: Gibberellin A4+7 (GA4:GA7=65:35)
• Synonyms: Gibberellin A4+7 (GA4:GA7=65:35)
• CAS NO: 668-44-0
• Molecular Formula: C₅H₃F₃N₄O₃
• Molecular Weight: 224.0975296
• Mol File: 668-44-0.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 185.8°C at 760 mmHg
• Flash Point: 66.1°C
• Appearance: /
• Density: 2.08g/cm³
• Vapor Pressure: 0.686mmHg at 25°C
• Refractive Index: 1.618
• PKA: 4.24±0.50(Predicted)
• CAS DataBase Reference: Gibberellin A4+7 (GA4:GA7=65:35)(CAS DataBase Reference)
• NIST Chemistry Reference: Gibberellin A4+7 (GA4:GA7=65:35)(668-44-0)
• EPA Substance Registry System: Gibberellin A4+7 (GA4:GA7=65:35)(668-44-0)

Safety Data

• Hazardous Substances Data: 668-44-0(Hazardous Substances Data)

Usage

Uses

Used in Horticulture:
Used in Agriculture:
Used in Plant Research:

InChI:InChI=1/C5H3F3N4O3/c6-5(7,8)4-10-2(9)1(12(14)15)3(13)11-4/h(H3,9,10,11,13)

Synthetic route

6-amino-4-hydroxy-2-trifluoromethylpyrimidine (1513-70-8) → 6-amino-4-hydroxy-5-nitro-2-trifluoromethylpyrimidine (668-44-0)

Conditions	Yield
With sulfuric acid; nitric acid at 55℃; for 1h;	95%

6-amino-4-hydroxy-5-nitro-2-trifluoromethylpyrimidine (668-44-0) → 5,6-diamino-4-hydroxy-2-trifluoromethylpyrimidine (672-50-4)

Conditions	Yield
With palladium 10% on activated carbon; hydrogen In ethanol; cyclohexene at 65℃; for 48h;	97%

6-amino-4-hydroxy-5-nitro-2-trifluoromethylpyrimidine (668-44-0) → C25H29F3N4O3

Conditions	Yield
Multi-step reaction with 2 steps 1: palladium 10% on activated carbon; hydrogen / ethanol; cyclohexene / 48 h / 65 °C 2: hydrogenchloride / water; ethanol / Reflux View Scheme

6-amino-4-hydroxy-5-nitro-2-trifluoromethylpyrimidine (668-44-0) → C25H28F3N5O3

Conditions	Yield
Multi-step reaction with 2 steps 1: palladium 10% on activated carbon; hydrogen / ethanol; cyclohexene / 48 h / 65 °C 2: hydrogenchloride / methanol; water / Reflux View Scheme

6-amino-4-hydroxy-5-nitro-2-trifluoromethylpyrimidine (668-44-0) → 2-((trans)-4-(4-(4-amino-7,7-dimethyl-2-(trifluoromethyl)-7H-pyrimido[4,5-b][1,4]oxazin-6-yl)phenyl)cyclohexyl)acetic acid

Conditions	Yield
Multi-step reaction with 3 steps 1: palladium 10% on activated carbon; hydrogen / ethanol; cyclohexene / 48 h / 65 °C 2: hydrogenchloride / water; ethanol / Reflux 3: sodium hydroxide / water; ethanol / 40 °C View Scheme

6-amino-4-hydroxy-5-nitro-2-trifluoromethylpyrimidine (668-44-0) → 2-((trans)-5′-(4-amino-7,7-dimethyl-2-(trifluoromethyl)-7Hpyrimido[4,5-b][1,4]oxazin-6-yl)-2′,3′-dihydrospiro-[cyclohexane-1,1′-inden]-4-yl)acetic acid

Conditions	Yield
Multi-step reaction with 3 steps 1: palladium 10% on activated carbon; hydrogen / ethanol; cyclohexene / 48 h / 65 °C 2: hydrogenchloride / methanol; water / Reflux 3: N,N-dimethyl-formamide / 24 h / 125 °C View Scheme

Upstream product

• 1513-70-8 6-amino-4-hydroxy-2-trifluoromethylpyrimidine 

Relevant articles and documents

Discovery of 6-phenylpyrimido[4,5- B ][1,4]oxazines as potent and selective Acyl CoA: Diacylglycerol acyltransferase 1 (DGAT1) inhibitors with in vivo efficacy in rodents

The discovery and optimization of a series of acyl CoA:diacylglycerol acyltransferase 1 (DGAT1) inhibitors based on a pyrimido[4,5-b][1,4]oxazine scaffold is described. The SAR of a moderately potent HTS hit was investigated resulting in the discovery of phenylcyclohexylacetic acid 1, which displayed good DGAT1 inhibitory activity, selectivity, and PK properties. During preclinical toxicity studies a metabolite of 1 was observed that was responsible for elevating the levels of liver enzymes ALT and AST. Subsequently, analogues were synthesized to preclude the formation of the toxic metabolite. This effort resulted in the discovery of spiroindane 42, which displayed significantly improved DGAT1 inhibition compared to 1. Spiroindane 42 was well tolerated in rodents in vivo, demonstrated efficacy in an oral triglyceride uptake study in mice, and had an acceptable safety profile in preclinical toxicity studies.