56-06-4

Basic information

• Product Name: 2,4-Diamino-6-hydroxypyrimidine
• Synonyms: TIMTEC-BB SBB004252;AKOS MSC-0109;2,4-DIAMINOPYRIMIDIN-6-OL;2,4-DIAMINO-6-HYDROXYPYRIMIDINE;2,4-DIAMINO-6-PYRIMIDINOL;2,4-DIAMINO-6(1H)-PYRIMIDINONE;2,6-DIAMINO-4-PYRIMIDINOL;2,6-DIAMINO-4-PYRIMIDINONE
• CAS NO: 56-06-4
• Molecular Formula: C₄H₆N₄O
• Molecular Weight: 126.12
• EINECS: 200-254-4
• Product Categories: PYRIMIDINE;APIs & Intermediate;Pyridines, Pyrimidines, Purines and Pteredines;Chemical Amines;13C & 2H Sugars;Amines;Bases & Related Reagents;Heterocycles;Nucleotides;Carbohydrates & Derivatives;Building Blocks;C4 to C5;Chemical Synthesis;Heterocyclic Building Blocks;Pyrimidines
• Mol File: 56-06-4.mol
• Article Data: 16

Chemical Properties

• Melting Point: 285-286 °C (dec.)(lit.)
• Boiling Point: 234.22°C (rough estimate)
• Flash Point: 128.3 °C
• Appearance: White to cream/Fine Crystalline Powder
• Density: 1.3659 (rough estimate)
• Vapor Pressure: 0.00232mmHg at 25°C
• Refractive Index: 1.7990 (estimate)
• Storage Temp.: Desiccate at +4°C
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 10.61±0.50(Predicted)
• Sensitive: Light Sensitive
• Merck: 14,2981
• BRN: 125006
• CAS DataBase Reference: 2,4-Diamino-6-hydroxypyrimidine(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4-Diamino-6-hydroxypyrimidine(56-06-4)
• EPA Substance Registry System: 2,4-Diamino-6-hydroxypyrimidine(56-06-4)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 22-24/25-36-26
• WGK Germany: 3
• TSCA: Yes
• Hazardous Substances Data: 56-06-4(Hazardous Substances Data)

Usage

Description

2,4-Diamino-6-hydroxypyrimidine (DAHP) is a selective, specific inhibitor of GTP cyclohydrolase I, the rate limiting step for de novo pterin synthesis. In HUVEC cells, the IC50 for inhibition of BH4 biosynthesis is about 0.3 mM. DAHP can be used to effectively block NO production in several cell types.

Chemical Properties

White Solid

Uses

2,4-Diamino-6-hydroxypyrimidine (DAHP) is a selective, specific inhibitor of GTP cyclohydrolase I, the rate limiting step for de novo pterin synthesis. In HUVEC cells, the IC50 for inhibition of BH4 biosynthesis is about 0.3 mM. DAHP can be used to effectively block NO production in several cell types.[Cayman Chemical]

Uses

It stands at the beginning of the enzyme-catalyzed cascade that starts with this seven-carbon carbohydrate and ends with the aromatic amino acids phenylalanine, tyrosine, and tryptophan

Uses

2,4-Diamino-6-hydroxypyrimidine (cas# 56-06-4) is a compound useful in organic synthesis.

Purification Methods

It recrystallises from H2O. [Beilstein 25 III/IV 3642.]

InChI:InChI=1/C4H6N4O.H2O4S/c5-2-1-3(9)8-4(6)7-2;1-5(2,3)4/h1H,(H5,5,6,7,8,9);(H2,1,2,3,4)

Synthetic route

guanidine nitrate (506-93-4) + ethyl 2-cyanoacetate (105-56-6) → 2,6-diaminopyrimidin-4-ol (56-06-4)

Conditions	Yield
Stage #1: guanidine nitrate; ethyl 2-cyanoacetate With sodium methylate In methanol for 4h; Reflux; Stage #2: With hydrogenchloride In water pH=9; pH-value;	95%

guanidine nitrate (113-00-8) + ethyl 2-cyanoacetate (105-56-6) → 2,6-diaminopyrimidin-4-ol (56-06-4)

Conditions	Yield
With triethylamine In ethanol for 4h; Reflux;	66%

2,4-diamino-5-formyl-6-oxo(1H)-pyrimidine (88075-70-1) → 2,6-diaminopyrimidin-4-ol (56-06-4)

Conditions	Yield
With sulfuric acid In methanol for 72h; Ambient temperature;

thiophenol (108-98-5) + NU6038 (100061-59-4) → Benzyl phenyl sulfide (831-91-4) + 2,6-diaminopyrimidin-4-ol (56-06-4)

Conditions	Yield
With triethylamine In methanol at 60℃; Rate constant;

2,4-diamino-6-fluoropyrimidine (696-83-3) → 2,6-diaminopyrimidin-4-ol (56-06-4)

Conditions	Yield
With sodium hydroxide In methanol; water at 20℃; Rate constant;

formamide (77287-34-4, 77287-35-5, 60100-09-6) → pyrimidine-4(3H)-one (51953-18-5) + 2,4-diaminopyrimidine (156-81-0) + parabanic acid (120-89-8) + isocytosine (108-53-2) + Cytosine (71-30-7) + oxalic acid (144-62-7) + guanidine nitrate (113-00-8) + 2-oxo-propionic acid (127-17-3) + uracil (66-22-8) + 2,6-diaminopyrimidin-4-ol (56-06-4) + 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) + urea (57-13-6) + glycine (56-40-6)

Conditions	Yield
With copper(II) choride dihydrate In water at 80℃; for 24h; pH=7.57;	A 5.6 mg B 0.3 mg C 0.59 mg D 5 mg E 0.13 mg F 0.1 mg G 1.6 mg H 0.0018 mg I 3.8 mg J 0.3 mg K 0.01 mg L 1.7 mg M 0.76 mg

...Expand

formamide (77287-34-4, 77287-35-5, 60100-09-6) → pyrimidine-4(3H)-one (51953-18-5) + 2,4-diaminopyrimidine (156-81-0) + guanidine nitrate (113-00-8) + uracil (66-22-8) + 2,6-diaminopyrimidin-4-ol (56-06-4) + urea (57-13-6)

Conditions	Yield
With manganese(II) chloride tetrahydrate In water at 80℃; for 24h; pH=7.57;	A 0.3 mg B 0.02 mg C 0.1 mg D 0.03 mg E 0.06 mg F 0.005 mg

guanidine nitrate (506-93-4) + methyl 2-cyanoacetate (105-34-0) → 2,6-diaminopyrimidin-4-ol (56-06-4)

Conditions	Yield
With sodium methylate

formamide (77287-34-4, 77287-35-5, 60100-09-6) → pyrimidine-4(3H)-one (51953-18-5) + guanazole (1455-77-2) + parabanic acid (120-89-8) + LACTIC ACID (849585-22-4) + 2-amino-1,9-dihydro-6H-purin-6-one (73-40-5) + Oxalacetic acid (328-42-7) + formylglycine (2491-15-8) + succinic acid (110-15-6) + Cytosine (71-30-7) + purine (120-73-0) + oxalic acid (144-62-7) + guanidine nitrate (113-00-8) + 2-oxo-propionic acid (127-17-3) + uracil (66-22-8) + 2,6-diaminopyrimidin-4-ol (56-06-4) + 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) + urea (57-13-6) + glycine (56-40-6) + rac-Ala-OH (302-72-7) + 2,4-diamino-pyrimidine-5-carboxylic acid (18588-61-9) + isocytosine

Conditions	Yield
With ferric sulfate nonahydrate; water at 80℃; for 24h;

...Expand

formamide (77287-34-4, 77287-35-5, 60100-09-6) → glycolaldehyde dimer (23147-58-2, 110822-84-9, 110822-85-0) + guanazole (1455-77-2) + LACTIC ACID (849585-22-4) + Oxalacetic acid (328-42-7) + succinic acid (110-15-6) + purine (120-73-0) + oxalic acid (144-62-7) + uracil (66-22-8) + 2,6-diaminopyrimidin-4-ol (56-06-4) + urea (57-13-6)

Conditions	Yield
With copper(II) chloride tetrahydrate; water at 80℃; for 24h;

...Expand

formamide (77287-34-4, 77287-35-5, 60100-09-6) → pyrimidine-4(3H)-one (51953-18-5) + parabanic acid (120-89-8) + 2-amino-1,9-dihydro-6H-purin-6-one (73-40-5) + Oxalacetic acid (328-42-7) + succinic acid (110-15-6) + oxalic acid (144-62-7) + 2-oxo-propionic acid (127-17-3) + 2,6-diaminopyrimidin-4-ol (56-06-4) + urea (57-13-6) + 2,4-diamino-pyrimidine-5-carboxylic acid (18588-61-9) + 2,3-diaminomaleonitrile (18514-52-8)

Conditions	Yield
With water; manganese(ll) chloride at 80℃; for 24h;

...Expand

malonic acid (141-82-2) + guanidine nitrate (113-00-8) + urea (57-13-6) → 2,4,6-triaminopyrimidine (1004-38-2) + 2-aminopyrimidine-4,6-diol (4425-67-6) + BARBITURIC ACID (67-52-7) + 2,4,6-triamino-s-triazine (108-78-1) + pyrimidine-2,4,5-triamine (3546-50-7) + C4H4N2O3*C4H5N3O2 + 2,6-diaminopyrimidin-4-ol (56-06-4) + 2-hydroxy-4,6-diaminopyrimidine (31458-45-4) + Malonamic acid (2345-56-4)

Conditions	Yield
at 65℃; for 120h;

...Expand

guanidine hydrochloride (50-01-1) + ethyl 2-cyanoacetate (105-56-6) → 2,6-diaminopyrimidin-4-ol (56-06-4)

Conditions	Yield
With sodium ethanolate In ethanol at 50 - 70℃; under 1500.15 Torr; for 1.5h; Large scale;

4-Cyanophenacyl bromide (20099-89-2) + 2,6-diaminopyrimidin-4-ol (56-06-4) → 4-(2-amino-4-hydroxy-7H-pyrrolo[2,3-d]pyrimidin-6-yl)benzonitrile

Conditions	Yield
Stage #1: 2,6-diaminopyrimidin-4-ol With sodium acetate In water at 100℃; for 0.333333h; Stage #2: 4-Cyanophenacyl bromide In methanol at 100℃;	100%
Stage #1: 2,6-diaminopyrimidin-4-ol With sodium acetate In water at 100℃; for 0.333333h; Stage #2: 4-Cyanophenacyl bromide In methanol; water at 100℃;	100%

potassium thioacyanate (333-20-0) + 2,6-diaminopyrimidin-4-ol (56-06-4) → 2,4-diamino-6-hydroxy-5-thiocyanatopyrimidine (22288-75-1)

Conditions	Yield
Stage #1: potassium thioacyanate; 2,6-diaminopyrimidin-4-ol With acetic acid at 25 - 95℃; Inert atmosphere; Stage #2: With bromine at 10 - 20℃; for 2h;	100%

o-chlorobenzylidene malononitrile (2698-41-1) + 2,6-diaminopyrimidin-4-ol (56-06-4) → 2,7-diamino-3,4-dihydro-4-oxo-5-(2-chlorophenyl)pyrido[2,3-d]pyrimidine-6-carbonitrile

Conditions	Yield
With N-benzyl-N,N,N-triethylammonium chloride In water at 90℃; for 5h;	99%

2,6-diaminopyrimidin-4-ol (56-06-4) → 5-bromo-2,4-diamino-6-hydroxypyrimidine (6312-72-7)

Conditions	Yield
With bromine; sodium hydrogencarbonate In methanol; water 2 h stirring, then standing overnight;	97%
With N-Bromosuccinimide; montmorillonite K-10; tetrabutylammomium bromide for 0.0416667h; microwave irradiation;	92%

2,6-diaminopyrimidin-4-ol (56-06-4) → 2,4-diamino-5-nitroso-6-hydroxypyrimidine (2387-48-6)

Conditions	Yield
With acetic acid; sodium nitrite In water at 80℃;	97%
With acetic acid; sodium nitrite In water	97%

2,6-diaminopyrimidin-4-ol (56-06-4) → 2,4-diamino-5-nitro-6-hydroxypyrimidine (3346-23-4)

Conditions	Yield
With sulfuric acid; nitric acid at 30 - 35℃; for 2h;	96.4%
With sodium nitrite In water at 0 - 5℃; under 750.075 Torr; for 0.5h; Large scale;

2-hydroxymethylene-1-tetralone sodium salt (138911-94-1) + 2,6-diaminopyrimidin-4-ol (56-06-4) → 10-amino-8-oxo-9H-5,6-dihydrobenzopyrimido<5,4-b>quinoline

Conditions	Yield
With phosphoric acid at 100℃; for 90h;	95%

2,6-diaminopyrimidin-4-ol (56-06-4) + 3-methylbenzene-1,2-diol (488-17-5) → 2-amino-5-methyl-9H-pyrimido[4,5-b]indole-4,6,7-triol

Conditions	Yield
In aq. phosphate buffer at 20℃; pH=7; Electrolysis; Green chemistry;	95%

3-[(2-methyl-4-oxo-4H-chromen-8-yl)methylene]pentane-2,4-dione (959934-74-8) + 2,6-diaminopyrimidin-4-ol (56-06-4) → 8-(6-acetyl-2-amino-4-hydroxy-7-methyl-5,8-dihydropyrido[2,3-d]-pyrimidin-5-yl)-2-methyl-4H-chromen-4-one (959934-79-3)

Conditions	Yield
In isopropyl alcohol for 48h; Reflux; Inert atmosphere;	94%

2,6-difluorobenzaldehyde (437-81-0) + 2,6-diaminopyrimidin-4-ol (56-06-4) + malononitrile (109-77-3) → 2,7-diamino-5-(2,6-difluorophenyl)-4-oxo-3,4,5,8-tetrahydropyrido[2,3-d]pyrimidine-6-carbonitrile

Conditions	Yield
With silica-coated iron oxide nanomagnetic particles-bonded S-sulfonic acid In neat (no solvent) at 100℃; for 0.133333h;	94%

benzene-1,2-diol (120-80-9) + 2,6-diaminopyrimidin-4-ol (56-06-4) → 2-amino-9H-pyrimido[4,5-b]indole-4,6,7-triol

Conditions	Yield
In aq. phosphate buffer at 20℃; pH=7; Electrolysis; Green chemistry;	93%

3,4 difluorobenzaldehyde (34036-07-2) + 2,6-diaminopyrimidin-4-ol (56-06-4) + malononitrile (109-77-3) → 2,7-diamino-5-(3,4-difluorophenyl)-4-oxo-3,4,5,8-tetrahydropyrido[2,3-d]pyrimidine-6-carbonitrile

Conditions	Yield
With silica-coated iron oxide nanomagnetic particles-bonded S-sulfonic acid In neat (no solvent) at 100℃; for 0.216667h;	92%

4-bromo-benzaldehyde (1122-91-4) + 2,6-diaminopyrimidin-4-ol (56-06-4) + malononitrile (109-77-3) → 2,7-diamino-5-(4-bromophenyl)-3,4,5,8-tetrahydro-4-oxopyrido[2,3-d]pyrimidine-6-carbonitrile

Conditions	Yield
With silica-coated iron oxide nanomagnetic particles-bonded S-sulfonic acid In neat (no solvent) at 100℃; for 0.183333h;	92%

europium(III) nitrate hydrate + 2,6-diaminopyrimidin-4-ol (56-06-4) → Eu((NH2)2C4N2H2O)2(H2O)3(NO3)2(1+)*NO3(1-)=Eu((NH2)2C4N2H2O)2(H2O)3(NO3)3 (857036-63-6)

Conditions	Yield
In methanol pyrimidine-compound was added to methanol, then hydrated Eu(NO3)3 was added, the soln. was stirred for 24 h; slow evapd.; elem. anal.;	91%

3-methocycatechol (934-00-9) + 2,6-diaminopyrimidin-4-ol (56-06-4) → 2-amino-5-methoxy-9H-pyrimido[4,5-b]indole-4,6,7-triol

Conditions	Yield
In aq. phosphate buffer at 20℃; pH=7; Electrolysis; Green chemistry;	91%

4-chlorobenzaldehyde (104-88-1) + 2,6-diaminopyrimidin-4-ol (56-06-4) + malononitrile (109-77-3) → 2,7-diamino-5-(4-chlorophenyl)-3,4,5,8-tetrahydro-4-oxopyrido[2,3-d]pyrimidine-6-carbonitrile

Conditions	Yield
With silica-coated iron oxide nanomagnetic particles-bonded S-sulfonic acid In neat (no solvent) at 100℃; for 0.166667h;	91%

4-cyanobenzaldehyde (105-07-7) + 2,6-diaminopyrimidin-4-ol (56-06-4) + malononitrile (109-77-3) → 2,7-diamino-5-(4-cyanophenyl)-4-oxo-3,4,5,8-tetrahydropyrido[2,3-d]pyrimidine-6-carbonitrile

Conditions	Yield
With silica-coated iron oxide nanomagnetic particles-bonded S-sulfonic acid In neat (no solvent) at 100℃; for 0.216667h;	91%

terbium(III) chloride hydrate + 2,6-diaminopyrimidin-4-ol (56-06-4) → Tb((NH2)2C4N2H2O)2(H2O)6(3+)*3Cl(1-)=Tb((NH2)2C4N2H2O)2(H2O)6Cl3

Conditions	Yield
In methanol pyrimidine-compound was added to methanol, then hydrated TbCl3 was added, the soln. was stirred for 24 h; slow evapd.; elem. anal.;	90.4%

4-Nitrobenzylidenemalononitrile (2700-23-4) + 2,6-diaminopyrimidin-4-ol (56-06-4) → 2,7-diamino-3,4-dihydro-4-oxo-5-(4-nitrophenyl)pyrido[2,3-d]pyrimidine-6-carbonitrile

Conditions	Yield
With N-benzyl-N,N,N-triethylammonium chloride In water at 90℃; for 6h;	90%

benzaldehyde (100-52-7) + 2,6-diaminopyrimidin-4-ol (56-06-4) + malononitrile (109-77-3) → 2,7-diamino-4-oxo-5-phenyl-3,4,5,8-tetrahydropyrido[2,3-d]pyrimidine-6-carbonitrile

Conditions	Yield
With silica-coated iron oxide nanomagnetic particles-bonded S-sulfonic acid In neat (no solvent) at 100℃; for 0.3h;	90%

m-bromobenzoic aldehyde (3132-99-8) + 2,6-diaminopyrimidin-4-ol (56-06-4) + malononitrile (109-77-3) → 2,7-diamino-5-(3-bromophenyl)-4-oxo-3,4,5,8-tetrahydropyrido[2,3-d]pyrimidine-6-carbonitrile

Conditions	Yield
With silica-coated iron oxide nanomagnetic particles-bonded S-sulfonic acid In neat (no solvent) at 100℃; for 0.2h;	90%

2,6-dichlorobenzaldehyde (83-38-5) + 2,6-diaminopyrimidin-4-ol (56-06-4) + malononitrile (109-77-3) → 2,7-diamino-5-(2,6-dichlorophenyl)-4-oxo-3,4,5,8-tetrahydropyrido[2,3-d]pyrimidine-6-carbonitrile

Conditions	Yield
With silica-coated iron oxide nanomagnetic particles-bonded S-sulfonic acid In neat (no solvent) at 100℃; for 0.2h;	90%

C12H13NO4 + 2,6-diaminopyrimidin-4-ol (56-06-4) → C16H19N5O5

Conditions	Yield
In water; ethyl acetate at 50℃; for 24h;	90%

n-hexanoic anhydride (2051-49-2) + 2,6-diaminopyrimidin-4-ol (56-06-4) → N,N'-(6-hydroxypyrimidine-2,4-diyl)dihexanamide (1402591-91-6)

Conditions	Yield
for 4h; Reflux;	89%

2-chloro-benzaldehyde (89-98-5) + 2,6-diaminopyrimidin-4-ol (56-06-4) + malononitrile (109-77-3) → 2,7-diamino-5-(2-chlorophenyl)-3,4,5,8-tetrahydro-4-oxopyrido[2,3-d]pyrimidine-6-carbonitrile

Conditions	Yield
With silica-coated iron oxide nanomagnetic particles-bonded S-sulfonic acid In neat (no solvent) at 100℃; for 0.233333h;	89%

3-nitro-benzaldehyde (99-61-6) + 2,6-diaminopyrimidin-4-ol (56-06-4) + malononitrile (109-77-3) → 2,7-diamino-5-(3-nitrophenyl)-4-oxo-3,4-dihydropyrido[2,3-d]pyrimidine-6-carbonitrile

Conditions	Yield
With silica-coated iron oxide nanomagnetic particles-bonded S-sulfonic acid In neat (no solvent) at 100℃; for 0.266667h;	89%

4-hydroxy-3-ethoxybenzaldehyde (121-32-4) + 2,6-diaminopyrimidin-4-ol (56-06-4) + malononitrile (109-77-3) → 2,7-diamino-5-(3-ethoxy-4-hydroxyphenyl)-4-oxo-3,4,5,8-tetrahydropyrido[2,3-d]pyrimidine-6-carbonitrile

Conditions	Yield
With silica-coated iron oxide nanomagnetic particles-bonded S-sulfonic acid In neat (no solvent) at 100℃; for 0.333333h;	89%

2,6-diaminopyrimidin-4-ol (56-06-4) + (4RS)-4-ethyl-7,8-dihydro-4-hydroxy-7-dimethylaminomethylene-1H-pyrano<3,4-f>indolizine-3,6,10(4H)-trione (154597-38-3) → (4RS)-8-amino-4-ethyl-4-hydroxy-1H-pyrano<3'',4'':6',7'>indolizino<2',1':5,6>pyrido<2,3-d>pyrimidine-3,10,14(4H,9H,12H)-trione

Conditions	Yield
In acetic acid for 20h; Heating;	88%

3-(4-chlorophenyl)-1-phenylprop-2-en-1-one (956-04-7) + 2,6-diaminopyrimidin-4-ol (56-06-4) → 5-(4-chlorophenyl)-7-phenyl-4-oxo-5,8-dihydropyrido<2,3-d>pyrimidine

Conditions	Yield
With aluminum oxide; potassium fluoride In ethanol at 80℃; for 0.666667h;	88%

Upstream product

• 506-93-4 Guanidine nitrate 
• 105-34-0 Methyl cyanoacetate 

Downstream Products

• 56-08-6 2,4-DIAMINO-6-MERCAPTOPYRIMIDINE 
• 3270-97-1 2,6-DIAMINO-4-METHOXY PYRIMIDINE 

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