Product Name

  • Name

    4-Aminopyrazolo[3,4-d]pyrimidine

  • EINECS 219-174-6
  • CAS No. 2380-63-4
  • Article Data47
  • CAS DataBase
  • Density 1.612 g/cm3
  • Solubility Insoluble in water.
  • Melting Point >325 °C(lit.)
  • Formula C5H5N5
  • Boiling Point 431.088 °C at 760 mmHg
  • Molecular Weight 135.128
  • Flash Point 244.382 °C
  • Transport Information UN 2811 6.1/PG 3
  • Appearance Light tan solid
  • Safety 26-36/37/39-45-22
  • Risk Codes 25-36/37/38-23/24/25
  • Molecular Structure Molecular Structure of 2380-63-4 (4-Aminopyrazolo[3,4-d]pyrimidine)
  • Hazard Symbols ToxicT
  • Synonyms 1H-Pyrazolo[3,4-d]pyrimidine,4-amino- (6CI,7CI,8CI);1H-Pyrazolo[3,4-d]pyrimidin-4-ylamine;8-Aza-7-deazaadenine;NSC 1393;1H-Pyrazolo[3,4-d]pyrimidin-4-amine;
  • PSA 80.48000
  • LogP 0.51630

Synthetic route

3-Amino-4-cyanopyrazole
16617-46-2

3-Amino-4-cyanopyrazole

formamide
77287-34-4, 77287-35-5, 60100-09-6

formamide

4-Aminopyrazolo<3,4-d>pyrimidin
2380-63-4

4-Aminopyrazolo<3,4-d>pyrimidin

Conditions
ConditionsYield
at 180℃;100%
at 170℃; for 5h; Inert atmosphere;94%
for 1h; Reflux;93%
formamide
77287-34-4, 77287-35-5, 60100-09-6

formamide

3-amino-4-cyano-2H-pyrazole
16617-46-2

3-amino-4-cyano-2H-pyrazole

4-Aminopyrazolo<3,4-d>pyrimidin
2380-63-4

4-Aminopyrazolo<3,4-d>pyrimidin

Conditions
ConditionsYield
at 180℃; Inert atmosphere;95%
at 180℃; for 2h; Microwave irradiation;93%
at 180℃; for 2h; Microwave irradiation;93%
3-Amino-4-cyanopyrazole
16617-46-2

3-Amino-4-cyanopyrazole

4-Aminopyrazolo<3,4-d>pyrimidin
2380-63-4

4-Aminopyrazolo<3,4-d>pyrimidin

Conditions
ConditionsYield
In formamide87%
3-Amino-4-cyanopyrazole
16617-46-2

3-Amino-4-cyanopyrazole

A

lH-pyrazolo[3,4-d]pyrimidin-4-ylamine

lH-pyrazolo[3,4-d]pyrimidin-4-ylamine

B

4-Aminopyrazolo<3,4-d>pyrimidin
2380-63-4

4-Aminopyrazolo<3,4-d>pyrimidin

Conditions
ConditionsYield
In formamideA n/a
B 87%
formamidine acetic acid
3473-63-0

formamidine acetic acid

3-amino-4-cyano-2H-pyrazole
16617-46-2

3-amino-4-cyano-2H-pyrazole

4-Aminopyrazolo<3,4-d>pyrimidin
2380-63-4

4-Aminopyrazolo<3,4-d>pyrimidin

Conditions
ConditionsYield
at 120℃; for 45h; Temperature; Concentration; Inert atmosphere;84.1%
In ethanol for 5h; Reflux;75%
N1,N1-dimethyl-N2-[4-cyanopyrazol-5-yl]formamidine
78972-81-3

N1,N1-dimethyl-N2-[4-cyanopyrazol-5-yl]formamidine

4-Aminopyrazolo<3,4-d>pyrimidin
2380-63-4

4-Aminopyrazolo<3,4-d>pyrimidin

Conditions
ConditionsYield
With ammonium hydroxide for 5h; Heating;80%
4-Aminopyrazolo<3,4-d>pyrimidin
2380-63-4

4-Aminopyrazolo<3,4-d>pyrimidin

3-bromo-4-aminopyrazolo<3,4-d>pyrimidine
83255-86-1

3-bromo-4-aminopyrazolo<3,4-d>pyrimidine

Conditions
ConditionsYield
With N-Bromosuccinimide In N,N-dimethyl-formamide at 60℃; for 3h;100%
With N-Bromosuccinimide In N,N-dimethyl-formamide at 80℃; for 5h;92%
With N-Bromosuccinimide In N,N-dimethyl-formamide at 60℃;91%
4-Aminopyrazolo<3,4-d>pyrimidin
2380-63-4

4-Aminopyrazolo<3,4-d>pyrimidin

4-amino-3-iodo-1H-pyrazolo[3,4-d]pyrimidine
151266-23-8

4-amino-3-iodo-1H-pyrazolo[3,4-d]pyrimidine

Conditions
ConditionsYield
With N-iodo-succinimide In N,N-dimethyl-formamide at 80℃;100%
With N-iodo-succinimide In N,N-dimethyl-formamide at 80℃; for 5h;98%
With N-iodo-succinimide In N,N-dimethyl-formamide for 12h;97%
4-Aminopyrazolo<3,4-d>pyrimidin
2380-63-4

4-Aminopyrazolo<3,4-d>pyrimidin

Hexafluoroacetone
684-16-2

Hexafluoroacetone

2,2,4,4-tetrakis(trifluoromethyl)-2,8-dihydro<1,3,5>oxadiazino<3,4-c>pyrazolopyrimidine
125509-32-2

2,2,4,4-tetrakis(trifluoromethyl)-2,8-dihydro<1,3,5>oxadiazino<3,4-c>pyrazolopyrimidine

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 80℃; for 24h;95%
di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

4-Aminopyrazolo<3,4-d>pyrimidin
2380-63-4

4-Aminopyrazolo<3,4-d>pyrimidin

C15H21N5O4

C15H21N5O4

Conditions
ConditionsYield
With dmap In tetrahydrofuran at 20℃; Inert atmosphere;90%
[(3aR,4S,6R, 6aR)-2,2-dimethyl-6-vinyl-4,5,6,6a-tetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl] trifluoromethanesulfonate
1373333-65-3

[(3aR,4S,6R, 6aR)-2,2-dimethyl-6-vinyl-4,5,6,6a-tetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl] trifluoromethanesulfonate

4-Aminopyrazolo<3,4-d>pyrimidin
2380-63-4

4-Aminopyrazolo<3,4-d>pyrimidin

1-((3aS,4R,6R,6aR)-2,2-dimethyl-6-vinyltetrahydro-3aHcyclopenta[d][1,3]dioxol-4-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine

1-((3aS,4R,6R,6aR)-2,2-dimethyl-6-vinyltetrahydro-3aHcyclopenta[d][1,3]dioxol-4-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine

Conditions
ConditionsYield
Stage #1: 4-Aminopyrazolo<3,4-d>pyrimidin With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 0.5h; Mitsunobu Displacement;
Stage #2: [(3aR,4S,6R, 6aR)-2,2-dimethyl-6-vinyl-4,5,6,6a-tetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl] trifluoromethanesulfonate In dichloromethane; N,N-dimethyl-formamide; mineral oil at 20℃; for 16h; Mitsunobu Displacement;		88%
N-iodo-succinimide
516-12-1

N-iodo-succinimide

4-Aminopyrazolo<3,4-d>pyrimidin
2380-63-4

4-Aminopyrazolo<3,4-d>pyrimidin

4-amino-3-iodo-1H-pyrazolo[3,4-d]pyrimidine
151266-23-8

4-amino-3-iodo-1H-pyrazolo[3,4-d]pyrimidine

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 80℃; for 12h;86%
In N,N-dimethyl-formamide at 80℃; Concentration; Solvent;
4-phenoxyiodobenzene
2974-94-9

4-phenoxyiodobenzene

4-Aminopyrazolo<3,4-d>pyrimidin
2380-63-4

4-Aminopyrazolo<3,4-d>pyrimidin

3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine
330786-24-8

3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine

Conditions
ConditionsYield
With potassium tert-butylate In dimethyl sulfoxide at 120℃; for 24h; Inert atmosphere;82%
Cyclopentyl bromide
137-43-9

Cyclopentyl bromide

4-Aminopyrazolo<3,4-d>pyrimidin
2380-63-4

4-Aminopyrazolo<3,4-d>pyrimidin

1-cyclopentyl-1H-pyrazolo[3,4-d]pyrimidin-4-ylamine
21254-14-8

1-cyclopentyl-1H-pyrazolo[3,4-d]pyrimidin-4-ylamine

Conditions
ConditionsYield
With caesium carbonate In N,N-dimethyl-formamide at 110℃;80%
1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose
6974-32-9

1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose

4-Aminopyrazolo<3,4-d>pyrimidin
2380-63-4

4-Aminopyrazolo<3,4-d>pyrimidin

(2R,3R,4R,5R)-2-(4-amino-1H-pyrazolo[3,4-d]pyrimidin-1-yl)-5-((benzoyloxy)methyl)tetrahydrofuran-3,4-diyl dibenzoate
854020-39-6

(2R,3R,4R,5R)-2-(4-amino-1H-pyrazolo[3,4-d]pyrimidin-1-yl)-5-((benzoyloxy)methyl)tetrahydrofuran-3,4-diyl dibenzoate

Conditions
ConditionsYield
With boron trifluoride diethyl etherate In nitromethane for 2h; Heating;79%
With boron trifluoride diethyl etherate In nitromethane for 1.5h; Reflux;59%
With boron trifluoride diethyl etherate In nitromethane Reflux;42%
C16H18F4O5S

C16H18F4O5S

4-Aminopyrazolo<3,4-d>pyrimidin
2380-63-4

4-Aminopyrazolo<3,4-d>pyrimidin

1-((3aS,4R,6S,6aR)-6-(4-fluorobenzyl)-2,2-dimethyltetrahydro-4H-cyclopenta[d][1,3]dioxol-4-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine

1-((3aS,4R,6S,6aR)-6-(4-fluorobenzyl)-2,2-dimethyltetrahydro-4H-cyclopenta[d][1,3]dioxol-4-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine

Conditions
ConditionsYield
Stage #1: 4-Aminopyrazolo<3,4-d>pyrimidin With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 0.5h;
Stage #2: C16H18F4O5S In N,N-dimethyl-formamide; mineral oil at 20℃; for 2h;		78%
2'-Deoxyguanosine
961-07-9

2'-Deoxyguanosine

4-Aminopyrazolo<3,4-d>pyrimidin
2380-63-4

4-Aminopyrazolo<3,4-d>pyrimidin

4-amino-1-(2-deoxy-β-D-erythro-pentofuranosyl)-1H-pyrazolo[3,4-d]pyrimidine
17318-21-7

4-amino-1-(2-deoxy-β-D-erythro-pentofuranosyl)-1H-pyrazolo[3,4-d]pyrimidine

Conditions
ConditionsYield
With purine nucleoside phosphorylase at 50℃; pH=7; aq. phosphate buffer; Enzymatic reaction;77%
copper (II) carbonate hydroxide

copper (II) carbonate hydroxide

(carboxymethyl(4-methylbenzyl)amino)acetic acid
166826-77-3

(carboxymethyl(4-methylbenzyl)amino)acetic acid

water
7732-18-5

water

4-Aminopyrazolo<3,4-d>pyrimidin
2380-63-4

4-Aminopyrazolo<3,4-d>pyrimidin

[Cu2(N-(p-methylbenzyl)iminodiacetate)2(μ2-N1,N8-4-aminopyrazolo[3,4-d]pyrimidine)(water)2]*4water

[Cu2(N-(p-methylbenzyl)iminodiacetate)2(μ2-N1,N8-4-aminopyrazolo[3,4-d]pyrimidine)(water)2]*4water

Conditions
ConditionsYield
Stage #1: copper (II) carbonate hydroxide; (carboxymethyl(4-methylbenzyl)amino)acetic acid In water at 50℃;
Stage #2: water; 4-Aminopyrazolo<3,4-d>pyrimidin In isopropyl alcohol for 1h;		75%
...Expand
1-(tert-Butoxycarbonyl)-3-(methanesulfonyloxy)piperidine
129888-60-4

1-(tert-Butoxycarbonyl)-3-(methanesulfonyloxy)piperidine

4-Aminopyrazolo<3,4-d>pyrimidin
2380-63-4

4-Aminopyrazolo<3,4-d>pyrimidin

tert-butyl 3-(4-amino-1H-pyrazolo[3,4-d]pyrimidin-1-yl)piperidine-1-carboxylate
1374250-98-2

tert-butyl 3-(4-amino-1H-pyrazolo[3,4-d]pyrimidin-1-yl)piperidine-1-carboxylate

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 100℃;72%
Stage #1: 4-Aminopyrazolo<3,4-d>pyrimidin With sodium hydride In N,N-dimethyl-formamide; mineral oil at 20℃; for 0.5h;
Stage #2: 1-(tert-Butoxycarbonyl)-3-(methanesulfonyloxy)piperidine In N,N-dimethyl-formamide; mineral oil at 100℃; for 16h;		50%
[1,3]-dioxolan-2-one
96-49-1

[1,3]-dioxolan-2-one

4-Aminopyrazolo<3,4-d>pyrimidin
2380-63-4

4-Aminopyrazolo<3,4-d>pyrimidin

9-(2'-hydroxyethyl)adenine
100524-24-1

9-(2'-hydroxyethyl)adenine

Conditions
ConditionsYield
With sodium hydroxide In N,N-dimethyl-formamide for 2h; Heating;71%
copper (II) carbonate hydroxide

copper (II) carbonate hydroxide

water
7732-18-5

water

(carboxymethyl(4-fluorobenzyl)amino)acetic acid
1813-23-6

(carboxymethyl(4-fluorobenzyl)amino)acetic acid

4-Aminopyrazolo<3,4-d>pyrimidin
2380-63-4

4-Aminopyrazolo<3,4-d>pyrimidin

[Cu4(N-(p-fluorobenzyl)iminodiacetate)4(μ2-N8,N9-4-aminopyrazolo[3,4-d]pyrimidine)2(water)]*water

[Cu4(N-(p-fluorobenzyl)iminodiacetate)4(μ2-N8,N9-4-aminopyrazolo[3,4-d]pyrimidine)2(water)]*water

Conditions
ConditionsYield
Stage #1: copper (II) carbonate hydroxide; (carboxymethyl(4-fluorobenzyl)amino)acetic acid In water at 50℃;
Stage #2: water; 4-Aminopyrazolo<3,4-d>pyrimidin In isopropyl alcohol for 1h;		65%
...Expand
1-azido-2,3-epoxypropane
80044-09-3

1-azido-2,3-epoxypropane

4-Aminopyrazolo<3,4-d>pyrimidin
2380-63-4

4-Aminopyrazolo<3,4-d>pyrimidin

1-(4-Amino-pyrazolo[3,4-d]pyrimidin-1-yl)-3-azido-propan-2-ol

1-(4-Amino-pyrazolo[3,4-d]pyrimidin-1-yl)-3-azido-propan-2-ol

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 8h;64%
4-Aminopyrazolo<3,4-d>pyrimidin
2380-63-4

4-Aminopyrazolo<3,4-d>pyrimidin

phenylboronic acid
98-80-6

phenylboronic acid

N-phenyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine
99973-41-8

N-phenyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine

Conditions
ConditionsYield
With [2,2]bipyridinyl; copper diacetate; caesium carbonate In N,N-dimethyl-formamide at 60℃; for 12h; Chan-Lam Coupling;62%
1-methyl-piperazine
109-01-3

1-methyl-piperazine

formaldehyd
50-00-0

formaldehyd

4-Aminopyrazolo<3,4-d>pyrimidin
2380-63-4

4-Aminopyrazolo<3,4-d>pyrimidin

1-(N-methylpiperazinomethyl)-4-(N-methylpiperazinomethylamino)pyrazolo<3,4-d>pyrimidine
83255-90-7

1-(N-methylpiperazinomethyl)-4-(N-methylpiperazinomethylamino)pyrazolo<3,4-d>pyrimidine

Conditions
ConditionsYield
In water60%
...Expand
2'-deoxyuridine
951-78-0

2'-deoxyuridine

4-Aminopyrazolo<3,4-d>pyrimidin
2380-63-4

4-Aminopyrazolo<3,4-d>pyrimidin

4-amino-1-(2-deoxy-β-D-erythro-pentofuranosyl)-1H-pyrazolo[3,4-d]pyrimidine
17318-21-7

4-amino-1-(2-deoxy-β-D-erythro-pentofuranosyl)-1H-pyrazolo[3,4-d]pyrimidine

Conditions
ConditionsYield
With purine nucleoside phosphorylase In dimethyl sulfoxide at 50℃; for 72h; pH=7; aq. phosphate buffer; Enzymatic reaction;60%
at 37℃; for 16h; alginate gel-entrapped cells of auxotrophic thymine-dependent strain of E. coli, ammonium acetate buffer pH 5.7;
4-Aminopyrazolo<3,4-d>pyrimidin
2380-63-4

4-Aminopyrazolo<3,4-d>pyrimidin

benzyl alcohol
100-51-6

benzyl alcohol

N-benzyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine
58360-86-4

N-benzyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine

Conditions
ConditionsYield
With samarium diiodide; potassium tert-butylate In tetrahydrofuran; toluene at 140℃; for 1.5h; Microwave irradiation; Inert atmosphere;59%

4-Aminopyrazolo[3,4-d]pyrimidine Chemical Properties

IUPAC Name:1H-Pyrazolo[3,4-d]pyrimidin-4-amine
Synonyms: 4-Aminopyrazolo(3,4-d)pyrimidine ; 1H-Pyrazolo(3,4-d)pyrimidin-4-amine ; 1H-Pyrazolo(3,4-d)pyrimidine, 4-amino- ;1H-pyrazolo[3,4-d]pyrimidin-4-amine ; 1H-Pyrazolo[3,4-d]pyrimidin-4-ylamine ; 1H-Pyrazolo[3,4-d]pyrimidine, 4-amino-
Product Categories: Pyrimidine ;Pyridines, Pyrimidines, Purines and Pteredines;Heterocyclic Compounds;Heterocycles
Mol File: 2380-63-4.mol
Molecular Structure :
Molecular Formula: C5H5N5
Molecular Weight: 135.13
CAS NO: 2380-63-4
EINECS : 219-174-6
BRN : 5824
Mol File: 2380-63-4.mol
Index of Refraction: 1.837
Surface Tension: 122.7 dyne/cm
Density: 1.612 g/cm3
Flash Point: 244.4 °C
Enthalpy of Vaporization: 68.67 kJ/mol
Boiling Point: 431.1 °C at 760 mmHg
Vapour Pressure: 1.23E-07 mmHg at 25°C
Melting point: >325 °C(lit.)
Appearance: Pyrazoloadenine (CAS NO. 2380-63-4) is light tan solid.

4-Aminopyrazolo[3,4-d]pyrimidine Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
cat LDLo intravenous 100mg/kg (100mg/kg) LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES

GASTROINTESTINAL: CHANGES IN STRUCTURE OR FUNCTION OF SALIVARY GLANDS

KIDNEY, URETER, AND BLADDER: URINE VOLUME INCREASED		 Proceedings of the Society for Experimental Biology and Medicine. Vol. 93, Pg. 398, 1956.
mouse LD10 unreported 15mg/kg (15mg/kg) LIVER: OTHER CHANGES Progress in Medical Chemistry. Vol. 7, Pg. 69, 1970.
mouse LD50 intraperitoneal 181mg/kg (181mg/kg)   National Cancer Institute Screening Program Data Summary, Developmental Therapeutics Program. Vol. JAN1986,
mouse LD50 oral 180mg/kg (180mg/kg) SENSE ORGANS AND SPECIAL SENSES: CILIARY SPASM: EYE

SENSE ORGANS AND SPECIAL SENSES: PTOSIS: EYE

BEHAVIORAL: EXCITEMENT		 Proceedings of the Society for Experimental Biology and Medicine. Vol. 93, Pg. 398, 1956.
rat LD50 intraperitoneal 228mg/kg (228mg/kg) SENSE ORGANS AND SPECIAL SENSES: CILIARY SPASM: EYE

SENSE ORGANS AND SPECIAL SENSES: PTOSIS: EYE

BEHAVIORAL: EXCITEMENT		 Proceedings of the Society for Experimental Biology and Medicine. Vol. 93, Pg. 398, 1956.
rat LD50 oral 141mg/kg (141mg/kg) SENSE ORGANS AND SPECIAL SENSES: CILIARY SPASM: EYE

SENSE ORGANS AND SPECIAL SENSES: PTOSIS: EYE

BEHAVIORAL: EXCITEMENT		 Proceedings of the Society for Experimental Biology and Medicine. Vol. 93, Pg. 398, 1956.

4-Aminopyrazolo[3,4-d]pyrimidine Consensus Reports

Reported in EPA TSCA Inventory.

4-Aminopyrazolo[3,4-d]pyrimidine Safety Profile

Poison by ingestion and intraperitoneal routes. Mutation data reported. When heated to decomposition it emits toxic fumes of NOx.
Hazard Codes ToxicT
Risk Statements 36/37/38-23/24/25
R36/37/38: Pyrazoloadenine (CAS NO. 2380-63-4) is irritating to eyes, respiratory system and skin. 
R23/24/25:Toxic by inhalation, in contact with skin and if swallowed.
Safety Statements 26-36/37/39-45-22 
S22:Do not breathe dust. 
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S45:In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) 
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection.
RIDADR UN 2811 6.1/PG 3
WGK Germany 3
RTECS UR0717000
HazardClass 6.1
PackingGroup III

4-Aminopyrazolo[3,4-d]pyrimidine Specification

General Information: As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear.
Extinguishing Media: Use carbon dioxide or dry chemical. 
Handling: Avoid contact with skin and eyes. Do not breathe dust, vapor, mist, or gas.
Storage: Store Pyrazoloadenine (CAS NO. 2380-63-4) in a cool, dry place. Store in a tightly closed container.

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