49721-45-1

Basic information

• Product Name: 4,5,6-TRIAMINOPYRIMIDINE SULFATE
• Synonyms: 4,5,6-TRIAMINOPYRIMIDINE SULFATE;4,5,6-TRIAMINO PYRIMIDINE MONOSULFATE;4,5,6-TRIAMINOPYRIMIDINE SULFATE SALT;4,5,6-TRIAMINOPYRIMIDINE SULPHATE;4,5,6-pyrimidinetriamine,sulfate(1:1);pyrimidine-4,5,6-triamine sulphate (1:1);4,5,6-Triaminopyrimidine sulfate, 98+%;NSC 49184
• CAS NO: 49721-45-1
• Molecular Formula: C₄H₇N₅*H₂O₄S
• Molecular Weight: 223.21
• EINECS: 256-446-3
• Product Categories: Building Blocks;Heterocyclic Building Blocks;Pyrimidines;Biochemicals and Reagents;Nucleoside Analogs;Nucleosides, Nucleotides, Oligonucleotides
• Mol File: 49721-45-1.mol
• Article Data: 1

Chemical Properties

• Melting Point: >300 °C(lit.)
• Boiling Point: 406.2ºC at 760mmHg
• Flash Point: 228.5ºC
• Appearance: white to yellow/powder
• Density: 1.512g/cm3
• Vapor Pressure: 4.71E-17mmHg at 25°C
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: 4,5,6-TRIAMINOPYRIMIDINE SULFATE(CAS DataBase Reference)
• NIST Chemistry Reference: 4,5,6-TRIAMINOPYRIMIDINE SULFATE(49721-45-1)
• EPA Substance Registry System: 4,5,6-TRIAMINOPYRIMIDINE SULFATE(49721-45-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26
• WGK Germany: 3
• Hazardous Substances Data: 49721-45-1(Hazardous Substances Data)

Usage

Chemical Properties

White to light brown solid

General Description

4,5,6-Triaminopyrimidine sulfate was converted to 4,5,6-triaminopyrimidine sulfite by formylation with C13 labeled formic acid that was used in the preparation of adenine labeled with C13.

InChI:InChI=1/C4H7N5.H2O4S/c5-2-3(6)8-1-9-4(2)7;1-5(2,3)4/h1H,5H2,(H4,6,7,8,9);(H2,1,2,3,4)/p-2

Synthetic route

4,6-diamino-5-nitrosylpyrimidine (61908-15-4) → 4,5,6-triaminopyrimidine sulfate (49721-45-1)

Conditions	Yield
With sodium dithionite; sulfuric acid In water at 20 - 80℃;

carbon disulfide (75-15-0) + 4,5,6-triaminopyrimidine sulfate (49721-45-1) → 8-mercaptoadenine (7390-62-7)

Conditions	Yield
With water; sodium hydrogencarbonate In ethanol for 72h; Reflux; Inert atmosphere;	100%
With sodium hydrogencarbonate In ethanol; water for 3h; Reflux;	58%
With sodium hydrogencarbonate In ethanol for 72h; Heating;

(4-hydroxylphenyl)glyoxal (24645-80-5) + 4,5,6-triaminopyrimidine sulfate (49721-45-1) → 4-(4-amino-pteridin-7-yl)-phenol (677297-48-2)

Conditions	Yield
With sodium hydroxide In methanol; water	100%

4,5,6-triaminopyrimidine sulfate (49721-45-1) → 4,5,6-triaminopyrimidine (118-70-7)

Conditions	Yield
Stage #1: 4,5,6-triaminopyrimidine sulfate With sodium hydroxide; water at 80℃; Stage #2: With hydrogenchloride; water at 0 - 5℃; pH=7.0;	99%
With sodium hydroxide In water at 80℃;	3.69 g

bis(3-hydroxyphenyl)ethane-1,2-dione (63192-57-4) + 4,5,6-triaminopyrimidine sulfate (49721-45-1) → 6,7-bis(3-hydroxyphenyl)-pteridine-4-ylamine

Conditions	Yield
With sodium hydrogencarbonate In diethyl ether; water	94.8%

benzpyrene-6-carbaldehyde (13312-42-0) + 4,5,6-triaminopyrimidine sulfate (49721-45-1) → 8-(6-benzo[a]pyrenyl)adenine

Conditions	Yield
With air In dimethyl sulfoxide at 90℃; for 2h;	88%

acetamide (60-35-5) + 4,5,6-triaminopyrimidine sulfate (49721-45-1) → 8-methyl-9H-purin-6-ylamine (22387-37-7)

Conditions	Yield
at 230℃; for 6h;	82%
at 240℃; for 6h;	11%

4,5,6-triaminopyrimidine sulfate (49721-45-1) + 4-chlorobenzoyl chloride (586-75-4) → 4,6-diamino-5-<(4-bromobenzoyl)amino>pyrimidine (77071-06-8)

Conditions	Yield
With sodium hydroxide for 1h;	75%

7-methylbenzanthracene carboxaldehyde (7505-62-6) + 4,5,6-triaminopyrimidine sulfate (49721-45-1) → 8-(7-benz[a]anthracenyl)adenine

Conditions	Yield
With air In dimethyl sulfoxide at 90℃; for 2h;	75%

dibenzo[def,p]chrysene-10-carboxaldehyde (2869-59-2) + 4,5,6-triaminopyrimidine sulfate (49721-45-1) → 8-(10-dibenzo[def,p]chrysenyl)adenine

Conditions	Yield
With air In dimethyl sulfoxide at 90℃; for 2h;	75%

ethyl 2-ethoxy-2-iminoacetate (816-27-3) + 4,5,6-triaminopyrimidine sulfate (49721-45-1) → 4,6-Diamino-8H-pteridin-7-one

Conditions	Yield
In ethanol for 2h; Heating;	71%

pyrene-1-aldehyde (3029-19-4) + 4,5,6-triaminopyrimidine sulfate (49721-45-1) → 8-(1-pyrenyl)adenine

Conditions	Yield
With air In dimethyl sulfoxide at 90℃;	68%

4,5,6-triaminopyrimidine sulfate (49721-45-1) + 9-anthracene aldehyde (642-31-9) → 8-(9-anthracenyl)adenine

Conditions	Yield
With air In dimethyl sulfoxide at 90℃;	64%

(13C)-formic acid (1633-56-3) + 4,5,6-triaminopyrimidine sulfate (49721-45-1) → <8-13C>adenine (86967-48-8)

Conditions	Yield
With morpholine at 0 - 200℃; for 3h;	64%

carbon disulfide (75-15-0) + 4,5,6-triaminopyrimidine sulfate (49721-45-1) → 6-amino-7,9-dihydro-8H-purine-8-thione (7390-62-7)

Conditions	Yield
With sodium hydrogencarbonate In ethanol; water at 80℃; for 48h;	56%

2-Picolinic acid (98-98-6) + 4,5,6-triaminopyrimidine sulfate (49721-45-1) → 8-(2-pyridin-2-yl)adenine (127820-09-1)

Conditions	Yield
at 150℃;	51%

4,5,6-triaminopyrimidine sulfate (49721-45-1) + hexanoic acid (142-62-1) → 8-n-pentyladenine (127820-07-9)

Conditions	Yield
With PPA at 150℃; for 2.5h;	42%

1-naphthalenecarboxylic acid (86-55-5) + 4,5,6-triaminopyrimidine sulfate (49721-45-1) → 8-(1-naphthyl)adenine (127820-10-4)

Conditions	Yield
at 150℃;	33%

4,5,6-triaminopyrimidine sulfate (49721-45-1) + 1-hexadecylcarboxylic acid (57-10-3) → 8-Pentadecyl-9H-purin-6-ylamine (127820-08-0)

Conditions	Yield
at 150℃;	33%

2-bromo-1-(3-trifluoromethylpyridin-2-yl)ethanone hydrobromide (832692-71-4) + 4,5,6-triaminopyrimidine sulfate (49721-45-1) → 7-(3-trifluoromethylpyridin-2-yl)pteridin-4-ylamine (1220632-19-8)

Conditions	Yield
Stage #1: 4,5,6-triaminopyrimidine sulfate With barium chloride monohydrate In water at 80℃; for 4h; Stage #2: 2-bromo-1-(3-trifluoromethylpyridin-2-yl)ethanone hydrobromide With sodium hydrogencarbonate In 1,4-dioxane; water at 20 - 100℃;	23%

4,5,6-triaminopyrimidine sulfate (49721-45-1) + 4-isothiocyanato-4-methylpentan-2-one (27248-25-5) → 4',6'-diamino-6-hydroxy-4,4,6-trimethyl-3,4,5,6-tetrahydro-[1,5']bipyrimidinyl-2-thione

Conditions	Yield
In methanol at 20℃; for 120h;	20%

4-isobutoxy-3-nitrobenzoyl chloride (528607-87-6) + 4,5,6-triaminopyrimidine sulfate (49721-45-1) → 4,6-Diamino-5-(4-isobutoxy-3-nitrobenzoyl)aminopyridine

Conditions	Yield
With sodium hydroxide In 1,4-dioxane; water at 0℃; for 4h;	20%

4,5,6-triaminopyrimidine sulfate (49721-45-1) + Trimethylacetic acid (75-98-9) → 8-tert-butyl-7(9)H-purin-6-ylamine (50609-20-6)

Conditions	Yield
at 150℃;	16%

4,5,6-triaminopyrimidine sulfate (49721-45-1) + naphthalene-2-carboxylate (93-09-4) → 8-Naphthalen-2-yl-9H-purin-6-ylamine (127820-11-5)

Conditions	Yield
at 150℃;	10%

heptafluorobutyramide (662-50-0) + 4,5,6-triaminopyrimidine sulfate (49721-45-1) → 8-(heptafluoropropyl)adenine

Conditions	Yield
at 200 - 210℃; for 5h;	7.3%

formic acid (64-18-6) + 4,5,6-triaminopyrimidine sulfate (49721-45-1) → N-(4,6-diaminopyrimidin-5-yl)formamide (5122-36-1)

Conditions	Yield
With water

4,5,6-triaminopyrimidine sulfate (49721-45-1) + formamide (77287-34-4, 77287-35-5, 60100-09-6) → 7H-purin-6-ylamine (73-24-5)

4,5,6-triaminopyrimidine sulfate (49721-45-1) + furil (492-94-4) → 6,7-di-furan-2-yl-pteridin-4-ylamine (30146-31-7)

Conditions	Yield
(i) BaCl2, H2O, (ii) /BRN= 383882/, dioxane; Multistep reaction;

ethyl 2-ethoxyglycolate (49653-17-0) + 4,5,6-triaminopyrimidine sulfate (49721-45-1) → 4-amino-7(8H)-pteridone (22005-66-9)

Conditions	Yield
With sodium 1) methanole, 15 min, room temperature, 2) 12 h, room temperature; Yield given. Multistep reaction;

4,5,6-triaminopyrimidine sulfate (49721-45-1) + benzoyl chloride (98-88-4) → N-(4,6-diamino-pyrimidin-5-yl)-benzamide (3298-83-7)

Conditions	Yield
In sodium hydroxide for 1h;

4,5,6-triaminopyrimidine sulfate (49721-45-1) + 4-methyl-benzoyl chloride (874-60-2) → N-(4,6-Diamino-pyrimidin-5-yl)-4-methyl-benzamide

Conditions	Yield
In sodium hydroxide for 1h;

Upstream product

• 61908-15-4 4,6-diamino-5-nitrosylpyrimidine 

Downstream Products

• 5122-36-1 N-(4,6-diaminopyrimidin-5-yl)formamide 
• 73-24-5 7H-purin-6-ylamine 
• 7390-62-7 8-mercaptoadenine 
• 7390-62-7 6-amino-7,9-dihydro-8H-purine-8-thione 
• 118-70-7 4,5,6-triaminopyrimidine 
• 73384-11-9 4-Amino-7-phenylpteridine 
• 50609-20-6 8-tert.-Butyl-9H-adenin 
• 77071-06-8 4,6-diamino-5-<(4-bromobenzoyl)amino>pyrimidine 
• 3298-83-7 4,6-Diamino-5-benzamido-pyrimidin 
• 22387-37-7 8-methyl-9H-purin-6-ylamine 
• 30146-31-7 4-Amino-6,7-bis(2-furyl)pteridin 

Relevant articles and documents

Synthesis of carbon-11-labeled imidazopyridine- and purine-thioacetamide derivatives as new potential PET tracers for imaging of nucleotide pyrophosphatase/phosphodiesterase 1 (NPP1)

The target tracer carbon-11-labeled imidazopyridine- and purine-thioacetamide derivatives, N-(3-[11C]methoxy-4-methoxyphenyl)-2-((5-methoxy-3H-imidazo[4,5-b]pyridin-2-yl)thio)acetamide (3-[11C]4a) and N-(4-[11C]methoxy-3-methoxyphenyl)-2-((5-methoxy-3H-imidazo[4,5-b]pyridin-2-yl)thio)acetamide (4-[11C]4a); 2-((6-amino-9H-purin-8-yl)thio)-N-(3-[11C]methoxy-4-methoxyphenyl)acetamide (3-[11C]8a) and 2-((6-amino-9H-purin-8-yl)thio)-N-(4-[11C]methoxy-3-methoxyphenyl)acetamide (4-[11C]8a), were prepared by O-[11C]methylation of their corresponding precursors with [11C]CH3OTf under basic condition (2 N NaOH) and isolated by a simplified solid-phase extraction (SPE) method in 50-60% radiochemical yields based on [11C]CO2 and decay corrected to end of bombardment (EOB). The overall synthesis time from EOB was 23 min, the radiochemical purity was >99%, and the specific activity at end of synthesis (EOS) was 185-555 GBq/μmol.