1904-98-9

Basic information

• Product Name: 2,6-Diaminopurine
• Synonyms: PYRIDINE-2,6-DIAMINE;TIMTEC-BB SBB004340;TIMTEC-BB SBB000103;2,6-DIAMINOPURINE;2,6-DIAMINO-9H-PURINE;26DAPY;1H-PURINE-2,6-DIAMINE;9H-PURINE-2,6-DIAMINE
• CAS NO: 1904-98-9
• Molecular Formula: C₅H₆N₆
• Molecular Weight: 150.14
• EINECS: 205-507-2
• Product Categories: AMINEPRIMARY;PYRIMIDINE;Pyridines, Pyrimidines, Purines and Pteredines;Purine;Amines;Purines;Amine Monomers;Monomers;Primary Amines
• Mol File: 1904-98-9.mol
• Article Data: 16

Chemical Properties

• Melting Point: 117-122 °C(lit.)
• Boiling Point: 285 °C(lit.)
• Flash Point: 155 °C
• Appearance: White to light yellow/Crystalline Powder or Granules
• Density: 1.2562 (rough estimate)
• Vapor Pressure: 3.65E-05mmHg at 25°C
• Refractive Index: 1.8750 (estimate)
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• PKA: 8.61±0.20(Predicted)
• Water Solubility: 2.38 g/L (20 ºC)
• Merck: 14,2985
• BRN: 9624
• CAS DataBase Reference: 2,6-Diaminopurine(CAS DataBase Reference)
• NIST Chemistry Reference: 2,6-Diaminopurine(1904-98-9)
• EPA Substance Registry System: 2,6-Diaminopurine(1904-98-9)

Safety Data

• Hazard Codes: Xn
• Statements: 22-36/37/38-40-20/21/22
• Safety Statements: 26-45-36/37-36/37/39-27-36-22
• WGK Germany: 3
• RTECS: US7570000
• F: 9
• TSCA: Yes
• Hazardous Substances Data: 1904-98-9(Hazardous Substances Data)

Usage

Chemical Properties

white to light yellow crystal powder

Uses

2,6-Diaminopurine can be used as analyte for biological and analytical studies of incorporation of unnatural nucleotides into mutant tRNA and proteins.

Definition

ChEBI: A member of the class of 2,6-diaminopurines that is 9H-purine in which the hydrogens at positions 2 and 6 are replaced by amino groups.

InChI:InChI=1/C5H6N6/c6-3-2-4(9-1-8-2)11-5(7)10-3/h1-2H,(H4,6,7,8,9,10,11)

Synthetic route

2,6-Diaminopurine hemisulfate (7280-83-3, 62043-11-2, 63041-03-2, 69369-16-0) → 2,6-diaminopurine (1904-98-9)

Conditions	Yield
With Dowex 50X8 (H-form) In water Ambient temperature;	92%

ethanol (64-17-5) + 2-azidoadenine (10536-81-9) → 8-ethoxy-2,6-diaminopurine (131287-56-4) + 2,6-diaminopurine (1904-98-9)

Conditions	Yield
Ambient temperature; Irradiation;	A 11% B 75%
Product distribution; Ambient temperature; Irradiation;	A 11% B 75%

2-azidoadenine (10536-81-9) → 2,6-diaminopurine (1904-98-9)

Conditions	Yield
In isopropyl alcohol Product distribution; Ambient temperature; Irradiation; or tert-butyl alcohol;	65%

methanol (67-56-1) + 2-azidoadenine (10536-81-9) → 8-methoxy-2,6-diaminopurine (131287-55-3) + 2,6-diaminopurine (1904-98-9)

Conditions	Yield
for 1.16667h; Ambient temperature; Irradiation;	A 37% B 37%
for 1.16667h; Product distribution; Ambient temperature; Irradiation;	A 37% B 37%

2,6 dichloropurine (5451-40-1) → 4-cyano-5-(cyanoamino)imidazole (85029-13-6) + 2-chloroadenine (1839-18-5) + 2,6-diaminopurine (1904-98-9)

Conditions	Yield
With potassium amide In ammonia at -33℃; for 20h;	A 25% B 12% C 13%

4-amidino-5-(cyanamino)imidazole (85029-14-7) → 2,6-diaminopurine (1904-98-9)

Conditions	Yield
Heating;

2-Amino-6-chloropurin (10310-21-1) → 4-cyano-5-(cyanoamino)imidazole (85029-13-6) + 2,6-diaminopurine (1904-98-9)

Conditions	Yield
With potassium amide In ammonia at -33℃; for 20h; Yield given. Yields of byproduct given;

9-(2-deoxy-α-L-erythro-pentofuranosyl)-2,6-diaminopurine → 2,6-diaminopurine (1904-98-9) + Phosphoric acid mono-((2S,4R,5S)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl) ester

Conditions	Yield
With E. coli purine nucleoside phosphorylase Enzyme kinetics; Substitution;

9-(2-deoxy-β-L-erythro-pentofuranosyl)-2,6-diaminopurine → 2,6-diaminopurine (1904-98-9) + Phosphoric acid mono-((2R,4R,5S)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl) ester

Conditions	Yield
With E. coli purine nucleoside phosphorylase Enzyme kinetics; Substitution;

4-cyano-5-(cyanoamino)imidazole (85029-13-6) → 2,6-diaminopurine (1904-98-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: KNH2 / liquid ammonia 2: Heating View Scheme

2-Amino-6-chloropurin (10310-21-1) → 2,6-diaminopurine (1904-98-9)

Conditions	Yield
Multi-step reaction with 3 steps 1: potassium amide / liquid ammonia / 20 h / -33 °C 2: KNH2 / liquid ammonia 3: Heating View Scheme

2,6 dichloropurine (5451-40-1) → 2,6-diaminopurine (1904-98-9)

Conditions	Yield
Multi-step reaction with 3 steps 1: 25 percent / potassium amide / liquid ammonia / 20 h / -33 °C 2: KNH2 / liquid ammonia 3: Heating View Scheme

2-amino-5'-deoxyadenosine → 2,6-diaminopurine (1904-98-9)

Conditions	Yield
adenosine phosphorilase In water pH=7.4; Enzymatic reaction; Phosphate buffer;

ethyl bromoacetate (105-36-2) → ethyl 2-[6-amino-2-{3-(t-butoxycarbonylamino)-propyl}amino-9H-purin-9-yl]acetate (1187357-51-2) + 2,6-diaminopurine (1904-98-9)

Conditions	Yield
With NaH In N,N-dimethyl-formamide; mineral oil

({[Mg4(adipate)4(N,N-dimethylacetamide)(H2O)]*5(N,N-dimethylacetamide)*2methanol*4H2O}) → 1-hydroxy-9H-xanthen-9-one (719-41-5) + 2,3,5-Trimethyl-1,4-benzoquinone (935-92-2) + 2-cyclopentylidenecyclopentan-1-one (825-25-2) + 2,6-diaminopurine (1904-98-9)

Conditions	Yield
at 330 - 400℃;

adenosine-2-amine (2096-10-8) → C5H9O8P(2-)*2K(1+) + 2,6-diaminopurine (1904-98-9)

Conditions	Yield
With potassium dihydrogenphosphate; E-purine nucleoside phosphorylase-0002 In aq. buffer at 40℃; for 0.233333h; pH=9; Equilibrium constant; Thermodynamic data; Temperature; Enzymatic reaction;

2-amino-2'-deoxyadenosine (4546-70-7) → C5H9O7P(2-)*2K(1+) + 2,6-diaminopurine (1904-98-9)

Conditions	Yield
With potassium dihydrogenphosphate; E-purine nucleoside phosphorylase-0002 In aq. buffer at 40℃; for 0.233333h; pH=9; Equilibrium constant; Thermodynamic data; Temperature; Enzymatic reaction;

(R)-glycidyl butyrate (60456-26-0) + 2,6-diaminopurine (1904-98-9) → Butyric acid (R)-3-(2,6-diamino-purin-9-yl)-2-hydroxy-propyl ester

Conditions	Yield
With caesium carbonate In N,N-dimethyl-formamide at 100℃; for 4h;	100%

2,6-diaminopurine (1904-98-9) + Acetic acid (3R,4S,5S)-2-acetoxy-4-benzyloxy-5-(tert-butyl-diphenyl-silanyloxymethyl)-5-(toluene-4-sulfonyloxymethyl)-tetrahydro-furan-3-yl ester (212970-74-6) → (2R,3R,4S,5S)-4-(benzyloxy)-5-((tert-butyldiphenylsilyloxy)methyl)-2-(2,6-diamino-9H-purin-9-yl)-5-(tosyloxymethyl)tetrahydrofuran-3-yl acetate (1341074-82-5)

Conditions

Yield

Stage #1: 2,6-diaminopurine; Acetic acid (3R,4S,5S)-2-acetoxy-4-benzyloxy-5-(tert-butyl-diphenyl-silanyloxymethyl)-5-(toluene-4-sulfonyloxymethyl)-tetrahydro-furan-3-yl ester With N,O-bis-(trimethylsilyl)-acetamide In acetonitrile at 65℃; for 1.5h; Inert atmosphere; Stage #2: With trimethylsilyl trifluoromethanesulfonate In acetonitrile at 0 - 65℃; for 3h; Vorbrüggen coupling; Inert atmosphere; Stage #3: With sodium hydrogencarbonate In water; acetonitrile Inert atmosphere;

100%

di-tert-butyl dicarbonate (24424-99-5) + 2,6-diaminopurine (1904-98-9) → 9,N2,N2,N6,N6-penta(Boc)-2,6-diaminopurine (1354832-39-5)

Conditions	Yield
With dmap In tetrahydrofuran at 0 - 20℃; for 18.0833h;	96%
With dmap In tetrahydrofuran at 0 - 20℃; for 18.08h; Inert atmosphere;	81%
With dmap In tetrahydrofuran at 20℃; for 18h;	76%

phenoxyacetic anhydride (14316-61-1) + 2,6-diaminopurine (1904-98-9) → N2,N6-bis(phenoxyacetyl)-2,6-diaminopurine

Conditions	Yield
In pyridine at 85℃; for 3h;	95%

2,6-diaminopurine (1904-98-9) + 2'-deoxy-2'-fluorouridine (56287-17-3, 69123-94-0, 784-71-4) → 2,6-diamino-9-(2-deoxy-2-fluoro-β-D-ribofuranosyl)-9H-purine (134444-47-6)

Conditions	Yield
In water at 37 - 50℃; for 48h; thymidine phosphorylase, purine nucleoside phosphorylase, phosphate buffer, pH 7;	94%
With E. coli BMT-4D Substitution;

iodobenzene (591-50-4) + 2,6-diaminopurine (1904-98-9) → 9-phenylpurine-2,6-diamine (6318-28-1)

Conditions	Yield
With N4,N7-bis(2-hydroxyethyl)-1,10-phenanthroline-4,7-diamine; sodium L-ascorbate; potassium hydroxide; copper(I) bromide In water; N,N-dimethyl-formamide at 120℃; for 21h; Inert atmosphere; Sealed tube; regioselective reaction;	94%

2,6-diaminopurine (1904-98-9) → isoguanine (6-amino-1H-purin-2(9H)-one) (3373-53-3)

Conditions	Yield
Stage #1: 2,6-diaminopurine With sodium hydroxide; sodium nitrite for 1h; Inert atmosphere; Stage #2: With sulfuric acid at 20 - 60℃; Inert atmosphere;	91%

water (7732-18-5) + 2,6-diaminopurine (1904-98-9) → 2,6-diaminopurine monohydrate (402846-48-4)

Conditions	Yield
Heating;	91%

5-bromo-2-chloro-4-methyl-6-morpholinopyrimidine (56035-66-6) + 2,6-diaminopurine (1904-98-9) → 9-(5-bromo-4-methyl-6-morpholinopyrimidin-2-yl)-9Hpurine-2,6-diamine

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide Reflux;	90%

4-(2-chloro-6-methylpyrimidin-4-yl)morpholine (52026-43-4) + 2,6-diaminopurine (1904-98-9) → 9-(4-methyl-6-morpholinopyrimidin-2-yl)-9H-purine-2,6-diamine

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide Reflux;	89%

2,6-diaminopurine (1904-98-9) → difluoropurine (1146697-82-6) + 2-fluoroadenine (700-49-2) + 2-Hydroxyadenine (3373-53-3)

Conditions	Yield
With tert.-butylnitrite In pyridine; hydrogen fluoride at 0℃; Kinetics; Balz-Schiemann Reaction; liquid HF; regioselective reaction;	A 8.8% B 88.5% C 0.5%

diethyl 2,2'-(sulfonylbis(4,1-phenylene)bis(oxy))diacetate (38775-52-9) + 2,6-diaminopurine (1904-98-9) → C42H32N12O12S2

Conditions	Yield
In ethanol at 80℃; Solvent;	87%

N,N'-bis(dimethylaminomethylene)hydrazine (16114-05-9) + 2,6-diaminopurine (1904-98-9) → 2-amino-6-(1,2,4-triazol-4-yl)-9-H-purine (306302-08-9)

Conditions	Yield
In N,N-dimethyl-formamide for 8h; Cycloaddition; Heating;	85%

araU (3083-77-0) + 2,6-diaminopurine (1904-98-9) → 2,6-diamino-9-(β-D-arabinofuranosyl)-purine (34079-68-0)

Conditions	Yield
With phosphate buffer; cell paste of Enterobacter aerogenes AJ 11125 at 60℃; for 15h; pH 7.0;	83%
With dipotassium hydrogenphosphate; sodium azide; purine nucleoside phodphorylase ( EC 2.4.2.1 ); uridine phosphorylase ( EC 2.4.2.3 ) at 37℃; for 288h; pH=7.1; Yield given;
With potassium phosphate; Geobacillus thermoglucosidasius purine nucleoside phosphorylase; Thermus thermophilus pyrimidine nucleoside phosphorylase In water at 70℃; for 3h; pH=7; Enzymatic reaction;

2,6-diaminopurine (1904-98-9) → 2-hydroxy-6-fluoro purine (1480-90-6) + 2,6-dihydroxypurine (69-89-6) + 2-Hydroxyadenine (3373-53-3)

Conditions	Yield
With tert.-butylnitrite; sulfuric acid; sodium fluoride In water at 25℃; Balz-Schiemann Reaction;	A n/a B n/a C 83%

2,6-diaminopurine (1904-98-9) → difluoropurine (1146697-82-6) + 2-hydroxy-6-fluoro purine (1480-90-6) + 2-fluoroadenine (700-49-2) + 2,6-dihydroxypurine (69-89-6)

Conditions	Yield
With tert.-butylnitrite In pyridine; hydrogen fluoride at 0℃; Reagent/catalyst; Solvent; Balz-Schiemann Reaction; liquid HF;	A 8% B n/a C 81% D n/a

2,6-diaminopurine (1904-98-9) + (1RS,5RS,8RS)-8-iodo-2-azabicyclo[3.3.1]nonan-3-one → (1RS,5RS,8RS)-8-(2,6-diamino-9H-purin-9-yl)-2-azabicyclo[3.3.1]nonan-3-one

Conditions	Yield
Stage #1: 2,6-diaminopurine With sodium hydride In N,N-dimethyl-formamide at 25℃; for 1h; Metallation; Stage #2: (1RS,5RS,8RS)-8-iodo-2-azabicyclo[3.3.1]nonan-3-one In N,N-dimethyl-formamide for 15h; Alkylation;	80%

ethyl bromoacetate (105-36-2) + 2,6-diaminopurine (1904-98-9) → Ethyl (2,6-diaminopurin-9-yl)acetate

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide Ambient temperature;	79%
With potassium carbonate In ethanol; N,N-dimethyl-formamide

1,5-anhydro-4,6-O-benzylidene-3-deoxy-2-O-[(4-methylphenyl)sulfonyl]-D-ribo-hexitol (149312-18-5) + 2,6-diaminopurine (1904-98-9) → 1’,5’-anhydro-4’,6’-O-benzylidene-2’,3’-dideoxy-2’-(2,6-diaminopurin-9-yl)-D-arabinohexitol

Conditions	Yield
Stage #1: 2,6-diaminopurine With sodium hydride In N,N-dimethyl-formamide; mineral oil at 20℃; for 0.5h; Inert atmosphere; Stage #2: 1,5-anhydro-4,6-O-benzylidene-3-deoxy-2-O-[(4-methylphenyl)sulfonyl]-D-ribo-hexitol In N,N-dimethyl-formamide; mineral oil at 20 - 90℃; for 12h; Inert atmosphere;	79%

2,6-diaminopurine (1904-98-9) → difluoropurine (1146697-82-6) + 2-hydroxy-6-fluoro purine (1480-90-6) + adenine (66224-66-6, 66224-67-7, 66224-68-8, 66224-69-9, 134434-48-3, 134434-49-4, 134454-76-5, 134461-75-9) + 2-fluoroadenine (700-49-2) + 2,6-dihydroxypurine (69-89-6)

Conditions	Yield
With tert.-butylnitrite; BF4(1-)*H3O(1+)*C4H10O In N,N-dimethyl-formamide at 0℃; Balz-Schiemann Reaction;	A 14% B n/a C 1% D 79% E n/a

2-oxiranylmethylisoindole-1,3-dione (5455-98-1) + 2,6-diaminopurine (1904-98-9) → 9-(3-phthalimido-2-hydroxypropyl)-2,6-diaminopurine (160308-67-8)

Conditions	Yield
With caesium carbonate In N,N-dimethyl-formamide at 120℃; for 6h;	78%

2,6-diaminopurine (1904-98-9) + N-(tert-Butyloxycarbonyl)-2-amino-2-propennitril → [1-Cyano-2-(2,6-diamino-purin-9-yl)-ethyl]-carbamic acid tert-butyl ester

Conditions	Yield
With potassium carbonate In dimethyl sulfoxide for 72h; Ambient temperature;	78%

O-phenyl N,N-diethylcarbamate (65009-00-9) + 2,6-diaminopurine (1904-98-9) → 9-phenylpurine-2,6-diamine (6318-28-1)

Conditions	Yield
With sodium t-butanolate In ethylene glycol at 100℃; for 12h;	78%

methanol (67-56-1) + hydrotris(3,5-methylphenylpyrazolyl)boratozinc(II) hydroxide + 2,6-diaminopurine (1904-98-9) → (HB(N2C3H(CH3)(C6H5))3)Zn(C5N6H5)*CH3OH

Conditions	Yield
In methanol; dichloromethane soln. Tp*Zn-OH complex in CH2Cl2 was added to suspn. nucleobase in MeOH and stirred for 4 h; react. mixt. was filtered and concd. and cooled to 0°C; elem. anal.;	77%

N-(3-chloropropyl)-3-<(tert-butoxycarbonylamino)-propionamido>propionamide (155177-69-8) + 2,6-diaminopurine (1904-98-9) → 2,6-diamino-9-<3-(3-(3-tert-butoxycarbonylamido)propionamido)-propionamido>propyl-9H-purine (155177-52-9)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 24h;	76%

3-methanesulfonyloxy-pyrrolidine-1-carboxylic acid tert-butyl ester (141699-57-2) + 2,6-diaminopurine (1904-98-9) → (RS)-9-(N-tert-butoxycarbonyl-3-pyrrolidinyl)-2,6-diaminopurine (898828-75-6)

Conditions	Yield
With caesium carbonate In dimethyl sulfoxide	76%

phenyl N,N-dimethylsulfamate (66950-63-8) + 2,6-diaminopurine (1904-98-9) → 9-phenylpurine-2,6-diamine (6318-28-1)

Conditions	Yield
With sodium t-butanolate In ethylene glycol at 100℃; for 12h;	76%

2,6-diaminopurine (1904-98-9) + ((2R,3S,4S)-3-(benzoyloxy)-5-bromo-4-fluorothiolan-2-yl)methyl benzoate (197647-17-9) → 9-(2-deoxy-3,5-di-O-benzoyl-2-fluoro-4-thio-α,β-D-arabino-pentofuranosyl)-2,6-diaminopurine (248601-55-0)

Conditions	Yield
With trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve In acetonitrile at 60℃; glycosylation;	75%

Upstream product

• 64-18-6 formic acid 
• 1006-23-1 5-nitroso-2,4,6-triaminopyrimidine 
• 77287-34-4 formamide 
• 10310-21-1 2-Amino-6-chloropurin 
• 5451-40-1 2,6 dichloropurine 
• 2096-10-8 adenosine-2-amine 
• 4546-70-7 2-amino-2'-deoxyadenosine 
• 105-36-2 ethyl bromoacetate 
• 85029-14-7 4-amidino-5-(cyanamino)imidazole 
• 7280-83-3 2,6-Diaminopurine hemisulfate 
• 10536-81-9 2-azidoadenine 
• 64-17-5 ethanol 
• 67-56-1 methanol 
• 593-85-1 diguanidine carbonate 

Downstream Products

• 18802-62-5 2,6,8-Triaminopurin 
• 51173-57-0 N,N'-(7⁽⁹⁾H-purine-2,6-diyl)-bis-benzamide 
• 34097-37-5 N,N'-(7(9)H-purine-2,6-diyl)-bis-acetamide 
• 7561-54-8 adenosine-2-amine 5'-(dihydrogen phosphate) 
• 84331-29-3 1-oxy-7(9)H-purine-2,6-diyldiamine 
• 72308-52-2 2,6-diamino-7,9-dihydro-purin-8-one 
• 30720-65-1 2,6-Diamino-9-methylpurine 
• 77071-04-6 8-(4-bromophenyl)adenine 
• 77071-05-7 8-(4-bromophenyl)-2,6-diaminopurine 
• 133119-17-2 (1S,2S,5S)-5-benzyloxymethyl-2-(2,6-diamino-9H-purin-9-yl)cyclopent-3-enol 
• 113852-35-0 (S)-(((1-(2,6-diamino-9H-purin-9-yl)-3-hydroxypropan-2-yl)oxy)methyl)phosphonic acid 
• 161452-62-6 (2R)-1,4-anhydro-3,5-di-O-benzyl-2-C-(2,6-diaminopurin-9-yl)-2-deoxy-D-arabitol 
• 161452-63-7 (2R,3R)-1,4-anhydro-5-O-benzyl-3-C-benzyloxymethyl-2-C-(2,6-diaminopurin-9-yl)-2,3-dideoxy-D-arabitol 
• 134444-47-6 2,6-diamino-9-(2-deoxy-2-fluoro-β-D-ribofuranosyl)-9H-purine 

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