56830-58-1

Basic information

• Product Name: 2,5-Diamino-4,6-dihydroxypyrimidine hydrochloride
• Synonyms: DADHP;DADHP X HCL;2,5-DIAMINOPYRIMIDINE-4,6-DIOL HCL;2,5-DIAMINOPYRIMIDINE-4,6-DIOL HYDROCHLORIDE;2,5-DIAMINO-4,6-DIHYDROXY PYRIMIDINE HCL;2,5-DIAMINO-4,6-DIHYDROXYPYRIMIDINE HYDROCHLORIDE;2,5-DIAMINO-4,6-DIHYDROXYPYRIMIDINE MONOHYDROCHLORIDE;2,5-diamino-6-hydroxy-3h-pyrimidin-4-one hydrochloride
• CAS NO: 56830-58-1
• Molecular Formula: C₄H₆N₄O₂*ClH
• Molecular Weight: 178.58
• EINECS: 433-170-3
• Product Categories: APIs & Intermediate;Pyrimidine;Amines
• Mol File: 56830-58-1.mol
• Article Data: 2

Chemical Properties

• Melting Point: >300 °C
• Boiling Point: 490 °C at 760 mmHg
• Flash Point: 250.1 °C
• Appearance: orange-pink powder
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• CAS DataBase Reference: 2,5-Diamino-4,6-dihydroxypyrimidine hydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: 2,5-Diamino-4,6-dihydroxypyrimidine hydrochloride(56830-58-1)
• EPA Substance Registry System: 2,5-Diamino-4,6-dihydroxypyrimidine hydrochloride(56830-58-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 37/39-26
• Hazardous Substances Data: 56830-58-1(Hazardous Substances Data)

Usage

Chemical Properties

orange-pink powder

Uses

Prasugrel? intermediate

Synthetic route

5-acetylamino-2-aminopyrimidine-4,6-diol → 2,5-Diamino-4,6-dihydroxypyrimidine hydrochloride (56830-58-1)

Conditions	Yield
With hydrogenchloride In water at 270℃; for 2h; Inert atmosphere;	49%

2,5-Diamino-4,6-dihydroxypyrimidine hydrochloride (56830-58-1) + methyl 4-(2-bromoacetyl)benzoate (56893-25-5) → 4-(2-Amino-4-oxo-3,7-dihydro-4H-pyrimido[4,5-b][1,4]oxazin-6-yl)-benzoic acid methyl ester (85828-45-1)

Conditions	Yield
With sodium hydrogencarbonate In methanol for 2h; Heating;	94%

3-(3-Methoxy-phenyl)-propionic acid (10516-71-9) + 2,5-Diamino-4,6-dihydroxypyrimidine hydrochloride (56830-58-1) → N-(2-amino-4,6-dihydroxypyrimidin-5-yl)-3-(3-methoxyphenyl)propanamide (1245319-69-0)

Conditions	Yield
Stage #1: 3-(3-Methoxy-phenyl)-propionic acid With thionyl chloride for 1h; Reflux; Stage #2: 2,5-Diamino-4,6-dihydroxypyrimidine hydrochloride With sodium hydroxide In 1,4-dioxane; water at 0 - 20℃; for 1h;	87%
Stage #1: 3-(3-Methoxy-phenyl)-propionic acid With thionyl chloride for 1h; Reflux; Stage #2: 2,5-Diamino-4,6-dihydroxypyrimidine hydrochloride With sodium hydroxide In 1,4-dioxane at 0 - 20℃; for 1h;	87%

3-(3-methoxyphenyl)propanoyl chloride (40478-49-7) + 2,5-Diamino-4,6-dihydroxypyrimidine hydrochloride (56830-58-1) → N-(2-amino-4,6-dihydroxypyrimidin-5-yl)-3-(3-methoxyphenyl)propanamide (1245319-69-0)

Conditions	Yield
With sodium hydroxide In 1,4-dioxane; water at 0 - 20℃; for 1h;	87%

2,5-Diamino-4,6-dihydroxypyrimidine hydrochloride (56830-58-1) → 2,5-diamino-4,6-dichloropyrimidine (55583-59-0)

Conditions	Yield
Stage #1: 2,5-Diamino-4,6-dihydroxypyrimidine hydrochloride With tetramethlyammonium chloride; trichlorophosphate In 1,2,3-trichloropropane at 115℃; for 24h; Stage #2: With sodium hydroxide In 1,2,3-trichloropropane; water at 50 - 60℃; for 0.5h; pH=6.5 - 7.0;	65%
With tetraethylammonium chloride; trichlorophosphate at 105℃; for 20h;	64%
With tetraethylammonium chloride; trichlorophosphate at 105℃; for 20h;	64%

N-ethyl-N-methyl piperidinium chloride (40215-83-6) + 2,5-Diamino-4,6-dihydroxypyrimidine hydrochloride (56830-58-1) → 2,5-diamino-4,6-dichloropyrimidine (55583-59-0)

Conditions	Yield
With trichlorophosphate	65%

2,5-Diamino-4,6-dihydroxypyrimidine hydrochloride (56830-58-1) + 4-(3-Bromo-2-oxo-propyl)-benzoic acid methyl ester (85828-56-4) → 2-amino-4-hydroxy-6-(p-carbomethoxybenzyl)-7,8-dihydro-8-oxapteridine (85828-57-5)

Conditions	Yield
With magnesium oxide In methanol for 4h; Heating;	50%

2,5-Diamino-4,6-dihydroxypyrimidine hydrochloride (56830-58-1) + N,N-dimethyl-formamide (68-12-2, 33513-42-7) → N-(2-amino-4,6-dichloropyrimidin-5-yl)formamide (171887-03-9)

Conditions	Yield
Stage #1: N,N-dimethyl-formamide With trichlorophosphate at 50℃; for 0.75h; Stage #2: 2,5-Diamino-4,6-dihydroxypyrimidine hydrochloride at 70 - 90℃; for 17.45 - 20.45h; Stage #3: With sodium hydroxide; water at 20 - 97℃; for 4 - 8h; pH=0.5 - 4.0; Product distribution / selectivity;	37.4%

2,5-Diamino-4,6-dihydroxypyrimidine hydrochloride (56830-58-1) + diethyl N--L-glutamate (85828-53-1) → diethyl N-<<(2-amino-4-hydroxy-7,8-dihydro-8-oxa-6-pteridinyl)methyl>benzoyl>-L-glutamate (85828-54-2)

Conditions	Yield
With magnesium oxide In methanol for 3h; Heating;	30%

1-chloro-3-phenylpropan-2-one (937-38-2) + 2,5-Diamino-4,6-dihydroxypyrimidine hydrochloride (56830-58-1) → 2-amino-6-benzyl-3,7-dihydro-pyrimido[4,5-b][1,4]oxazin-4-one (70080-71-6)

Conditions	Yield
With sodium hydrogencarbonate In ethanol Heating;

1-chloro-2-heptanone (41055-92-9) + 2,5-Diamino-4,6-dihydroxypyrimidine hydrochloride (56830-58-1) → 2-amino-6-pentyl-3,7-dihydro-pyrimido[4,5-b][1,4]oxazin-4-one (70080-74-9)

Conditions	Yield
With sodium hydrogencarbonate In ethanol Heating;

ethyl Bromopyruvate (70-23-5) + 2,5-Diamino-4,6-dihydroxypyrimidine hydrochloride (56830-58-1) → 2-amino-4-oxo-3,7-dihydro-4H-pyrimido[4,5-b][1,4]oxazine-6-carboxylic acid ethyl ester (73217-09-1)

Conditions	Yield
In ethanol Heating;

ethyl (2-chloroaceto)acetate (638-07-3) + 2,5-Diamino-4,6-dihydroxypyrimidine hydrochloride (56830-58-1) → (2-amino-4-oxo-3,5-dihydro-4H-pyrimido[4,5-b][1,4]oxazin-6-ylidene)-acetic acid ethyl ester (73217-06-8)

Conditions	Yield
In ethanol Heating;

1-chloro-5-phenyl-pentan-2-one (58009-85-1) + 2,5-Diamino-4,6-dihydroxypyrimidine hydrochloride (56830-58-1) → 2-amino-6-(3-phenyl-propyl)-3,7-dihydro-pyrimido[4,5-b][1,4]oxazin-4-one (70080-72-7)

Conditions	Yield
With sodium hydrogencarbonate In ethanol Heating;

1-chloro-4-phenylbutan-2-one (20845-80-1) + 2,5-Diamino-4,6-dihydroxypyrimidine hydrochloride (56830-58-1) → 2-amino-6-phenethyl-3,7-dihydro-pyrimido[4,5-b][1,4]oxazin-4-one (70080-77-2)

Conditions	Yield
With sodium hydrogencarbonate In ethanol Heating;

1-chloro-6-phenyl-hexan-2-one (70080-70-5) + 2,5-Diamino-4,6-dihydroxypyrimidine hydrochloride (56830-58-1) → 2-amino-6-(4-phenyl-butyl)-3,7-dihydro-pyrimido[4,5-b][1,4]oxazin-4-one (70080-73-8)

Conditions	Yield
With sodium hydrogencarbonate In ethanol Heating;

4,6-Dichloro-2,5-bis-[(dimethylamino)methyleneamino]pyrimidine + 2,5-Diamino-4,6-dihydroxypyrimidine hydrochloride (56830-58-1) → N-(2-amino-4,6-dichloropyrimidin-5-yl)formamide (171887-03-9)

Conditions	Yield
With sodium hydroxide; phosphoric acid; trichlorophosphate In N-methyl-acetamide; water; toluene

2,5-Diamino-4,6-dihydroxypyrimidine hydrochloride (56830-58-1) → N-(2-amino-4,6-dichloropyrimidin-5-yl)formamide (171887-03-9)

Conditions	Yield
With sodium hydroxide; trichlorophosphate In N-methyl-acetamide; water
With sodium hydroxide; trichlorophosphate In N-methyl-acetamide; water

triethylmethylammonium chloride (10052-47-8) + 2,5-Diamino-4,6-dihydroxypyrimidine hydrochloride (56830-58-1) → 2,5-diamino-4,6-dichloropyrimidine (55583-59-0)

Conditions	Yield
With sodium hydroxide; trichlorophosphate In ethyl acetate; acetonitrile

1,2,3-trichloropropane (96-18-4) + 2,5-Diamino-4,6-dihydroxypyrimidine hydrochloride (56830-58-1) → 2,5-diamino-4,6-dichloropyrimidine (55583-59-0)

Conditions	Yield
With sodium hydroxide; tetramethlyammonium chloride; trichlorophosphate In tetrahydrofuran; (2S)-N-methyl-1-phenylpropan-2-amine hydrate; hexane

3-(2-thienyl)-propanoic acid chloride (5834-04-8) + 2,5-Diamino-4,6-dihydroxypyrimidine hydrochloride (56830-58-1) → N-(2-amino-4,6-dihydroxypyrimidin-5-yl)-3-thiophen-2-yl-propionamide (1245318-71-1)

Conditions	Yield
With sodium hydroxide In water at 20℃; for 18h;
With sodium hydroxide In water
With sodium hydroxide In water at 20℃; for 18h;	1.25 g

Upstream product

• 6829-40-9 aminomalonic acid diethyl ester 
• 50-01-1 guanidine hydrochloride 

Downstream Products

• 73217-06-8 (2-amino-4-oxo-3,5-dihydro-4H-pyrimido[4,5-b][1,4]oxazin-6-ylidene)-acetic acid ethyl ester 
• 70080-72-7 2-amino-6-(3-phenyl-propyl)-3,7-dihydro-pyrimido[4,5-b][1,4]oxazin-4-one 
• 70080-77-2 2-amino-6-phenethyl-3,7-dihydro-pyrimido[4,5-b][1,4]oxazin-4-one 
• 70080-73-8 2-amino-6-(4-phenyl-butyl)-3,7-dihydro-pyrimido[4,5-b][1,4]oxazin-4-one 
• 55583-59-0 2,5-diamino-4,6-dichloropyrimidine 
• 85828-45-1 4-(2-Amino-4-oxo-3,7-dihydro-4H-pyrimido[4,5-b][1,4]oxazin-6-yl)-benzoic acid methyl ester 
• 85828-57-5 2-amino-4-hydroxy-6-(p-carbomethoxybenzyl)-7,8-dihydro-8-oxapteridine 
• 85828-54-2 diethyl N-<<(2-amino-4-hydroxy-7,8-dihydro-8-oxa-6-pteridinyl)methyl>benzoyl>-L-glutamate 
• 171887-03-9 N-(2-amino-4,6-dichloropyrimidin-5-yl)formamide 
• 1245319-69-0 N-(2-amino-4,6-dihydroxypyrimidin-5-yl)-3-(3-methoxyphenyl)propanamide 

Relevant articles and documents

Triazolopyrimidines identified as reversible myeloperoxidase inhibitors

Myeloperoxidase, a mammalian peroxidase involved in the immune system as an anti-microbial first responder, can produce hypochlorous acid in response to invading pathogens. Myeloperoxidase has been implicated in several chronic pathological diseases due to the chronic production of hypochlorous acid, as well as other reactive radical species. A high throughput screen and triaging protocol was developed to identify a reversible inhibitor of myeloperoxidase toward the potential treatment of chronic diseases such as atherosclerosis. The identification and characterization of a reversible myeloperoxidase inhibitor, 7-(benzyloxy)-3H-[1,2,3]triazolo[4,5-d]pyrimidin-5-amine is described.