2846-89-1

Basic information

• Product Name: 4,5-DIAMINO-6-MERCAPTOPYRIMIDINE
• Synonyms: 4,5-DIAMINO-6-MERCAPTOPYRIMIDINE;5,6-diaminopyrimidine-4-thiol;4(1H)-Pyrimidinethione, 5,6-diamino- (9CI);4,5-DIAMINO-6-THIOPYRIMIDINE;4,5-Diamino-6-mercaptopyrimidine ,97%;5,6-Diaminopyrimidine-4(1H)-thione;5,6-Diaminopyrimidine-4(3H)-thione
• CAS NO: 2846-89-1
• Molecular Formula: C₄H₆N₄S
• Molecular Weight: 142.18
• EINECS: 220-644-8
• Product Categories: PYRIMIDINE
• Mol File: 2846-89-1.mol
• Article Data: 2

Chemical Properties

• Melting Point: 257 °C (decomp)
• Boiling Point: 229.3 °C at 760 mmHg
• Flash Point: 92.5 °C
• Appearance: /
• Density: 1.78g/cm³
• Vapor Pressure: 0.07mmHg at 25°C
• Refractive Index: 1.85
• PKA: 5.87±0.20(Predicted)
• CAS DataBase Reference: 4,5-DIAMINO-6-MERCAPTOPYRIMIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 4,5-DIAMINO-6-MERCAPTOPYRIMIDINE(2846-89-1)
• EPA Substance Registry System: 4,5-DIAMINO-6-MERCAPTOPYRIMIDINE(2846-89-1)

Safety Data

• Safety Statements: 24/25
• Hazardous Substances Data: 2846-89-1(Hazardous Substances Data)

Usage

Chemical Properties

Light yellow solid

InChI:InChI=1/C4H6N4S/c5-2-3(6)7-1-8-4(2)9/h1H,5H2,(H3,6,7,8,9)

Synthetic route

4,5-diamino-6-hydroxypyrimidine (1672-50-0) → 4,5-Diamino-6-mercaptopyrimidine (2846-89-1)

Conditions	Yield
With Lawessons reagent	43%

2-chloro-4,6-dimethylnicotinonitrile (14237-71-9) + 4,5-Diamino-6-mercaptopyrimidine (2846-89-1) → 2-(5,6-diamino-pyrimidin-4-ylsulfanyl)-4,6-dimethyl-nicotinonitrile

Conditions	Yield
With sodium hydroxide In methanol for 20h; Heating;	96%

4,5-Diamino-6-mercaptopyrimidine (2846-89-1) + 2-chloro-5-nitrobenzaldehyde (6361-21-3) → 4-amino-8-nitropyrimido[4,5-b]-1,4-benzothiazepine

Conditions	Yield
With sodium hydroxide In methanol at 60 - 65℃;	93%

4-chloro-3-cyanonitrobenzene (16588-02-6) + 4,5-Diamino-6-mercaptopyrimidine (2846-89-1) → 2-(5,6-diamino-pyrimidin-4-ylsulfanyl)-5-nitro-benzonitrile

Conditions	Yield
With sodium hydroxide In methanol at 60 - 65℃; for 1h;	82%

4,5-Diamino-6-mercaptopyrimidine (2846-89-1) + 6-chloro-1,3-dimethyl-5-nitrouracil (1203-25-4) → 4-Amino-5,7-dimethyl-10,10a-dihydro-5H,8aH-9-thia-1,3,5,7,10-pentaaza-anthracene-6,8-dione (96090-27-6)

Conditions	Yield
	78%

2-Bromo-3-isopropylamino-5,5-dimethyl-cyclohex-2-enone (102689-02-1) + 4,5-Diamino-6-mercaptopyrimidine (2846-89-1) → N8-Isopropyl-6,6-dimethyl-6,10-dihydro-7H-9-thia-1,3,10-triaza-anthracene-4,8-diamine; hydrobromide

Conditions	Yield
	70%

4,5-Diamino-6-mercaptopyrimidine (2846-89-1) + urea (57-13-6) → C5H4N4OS

Conditions	Yield
Heating;	65%

2-Bromo-3-butylamino-5,5-dimethyl-cyclohex-2-enone (102688-96-0) + 4,5-Diamino-6-mercaptopyrimidine (2846-89-1) → N8-Butyl-6,6-dimethyl-6,10-dihydro-7H-9-thia-1,3,10-triaza-anthracene-4,8-diamine; hydrobromide

Conditions	Yield
	63%

3-Amino-2-bromo-5,5-dimethyl-cyclohex-2-enone (51924-68-6) + 4,5-Diamino-6-mercaptopyrimidine (2846-89-1) → 4,9-Diamino-7,7-dimethyl-7,8-dihydro-1,3-diazaphenothiazine hydrobromide

Conditions	Yield
	62.5%

3-Benzylamino-2-bromo-5,5-dimethyl-2-cyclohexen-1-one (51924-66-4) + 4,5-Diamino-6-mercaptopyrimidine (2846-89-1) → N8-Benzyl-6,6-dimethyl-6,10-dihydro-7H-9-thia-1,3,10-triaza-anthracene-4,8-diamine; hydrobromide

Conditions	Yield
	62%

4,5-Diamino-6-mercaptopyrimidine (2846-89-1) + acenaphthene quinone (82-86-0) → 6,7-acenaphtheno-4-thiopteridine (78241-70-0)

Conditions	Yield
In acetic acid for 2h; Heating;	62%

2-Bromo-3-heptylamino-5,5-dimethyl-cyclohex-2-enone (102688-99-3) + 4,5-Diamino-6-mercaptopyrimidine (2846-89-1) → N8-Heptyl-6,6-dimethyl-6,10-dihydro-7H-9-thia-1,3,10-triaza-anthracene-4,8-diamine; hydrobromide

Conditions	Yield
	58%

4,5-Diamino-6-mercaptopyrimidine (2846-89-1) + 9,10-phenanthrenequinone (84-11-7) → 6,7-phenanthreno-4-thiopteridine (78241-69-7)

Conditions	Yield
In acetic acid for 2h; Heating;	56%

2-Bromo-3-hexylamino-5,5-dimethyl-cyclohex-2-enone (102688-98-2) + 4,5-Diamino-6-mercaptopyrimidine (2846-89-1) → N8-Hexyl-6,6-dimethyl-6,10-dihydro-7H-9-thia-1,3,10-triaza-anthracene-4,8-diamine; hydrobromide

Conditions	Yield
	54%

4,5-Diamino-6-mercaptopyrimidine (2846-89-1) + 6-chloro-1,3-dimethyl-5-nitrouracil (1203-25-4) → 4-Amino-6,8-dimethyl-7,9-dioxo-9a-hydroxy-6,7,8,9-tetrahydrodipyrimido<4.5-b><4'.5'-e><1,4>thiazine + 4-Amino-6,8-dimethyl-7,9-dioxo-6,7,8,9-tetrahydrodipyrimido<4.5-b><4'.5'-e><1,4>thiazinyl (123625-47-8)

Conditions	Yield
With dihydrogen peroxide; triethylamine In methanol at 20℃; for 0.5h;	A 30% B 42%
With triethylamine In methanol at 20℃; for 0.5h;	A 30% B 42%

thiazole-4-carbonitrile (1452-15-9) + 4,5-Diamino-6-mercaptopyrimidine (2846-89-1) → 8-thiazol-4-yl-1,7(9)-dihydro-purine-6-thione (65911-27-5)

Conditions	Yield
With PPA at 180 - 210℃;

acetic anhydride (108-24-7) + 4,5-Diamino-6-mercaptopyrimidine (2846-89-1) → N-(2-methyl-thiazolo[5,4-d]pyrimidin-7-yl)-acetamide (108129-04-0)

chloroacetonitrile (107-14-2) + 4,5-Diamino-6-mercaptopyrimidine (2846-89-1) → 7H-pyrimido[4,5-b][1,4]thiazine-4,6-diamine (55383-58-9)

N-phenylsulfinylamine (222851-56-1) + 4,5-Diamino-6-mercaptopyrimidine (2846-89-1) → phenyl-[1,2,5]thiadiazolo[3,4-d]pyrimidin-7-yl-amine (6306-88-3)

Conditions	Yield
With pyridine

chloroacetic acid (79-11-8) + 4,5-Diamino-6-mercaptopyrimidine (2846-89-1) → 4-amino-5H-pyrimido[4,5-b][1,4]thiazin-6-one (120267-09-6)

4,5-Diamino-6-mercaptopyrimidine (2846-89-1) → [1,2,3]thiadiazolo[5,4-d]pyrimidin-7-ylamine (21323-67-1)

Conditions	Yield
With sulfuric acid; sodium nitrite

4,5-Diamino-6-mercaptopyrimidine (2846-89-1) → 6H-[1,2,5]thiadiazolo[3,4-d]pyrimidine-7-thione (89797-62-6)

Conditions	Yield
With pyridine; N-phenylsulfinylamine

4,5-Diamino-6-mercaptopyrimidine (2846-89-1) + (6R,7R)-3-((E)-3-Iodo-propenyl)-7-{2-[(Z)-methoxyimino]-2-[2-(trityl-amino)-thiazol-4-yl]-acetylamino}-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 4-methoxy-benzyl ester → (6R,7R)-3-[(E)-3-(5,6-Diamino-pyrimidin-4-ylsulfanyl)-propenyl]-7-{2-[(Z)-methoxyimino]-2-[2-(trityl-amino)-thiazol-4-yl]-acetylamino}-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 4-methoxy-benzyl ester

Conditions	Yield
In N,N-dimethyl-formamide

4,5-Diamino-6-mercaptopyrimidine (2846-89-1) + (6R,7R)-3-((E)-3-Iodo-propenyl)-8-oxo-7-{2-[(Z)-prop-2-ynyloxyimino]-2-[2-(trityl-amino)-thiazol-4-yl]-acetylamino}-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 4-methoxy-benzyl ester → (6R,7R)-3-[(E)-3-(5,6-Diamino-pyrimidin-4-ylsulfanyl)-propenyl]-8-oxo-7-{2-[(Z)-prop-2-ynyloxyimino]-2-[2-(trityl-amino)-thiazol-4-yl]-acetylamino}-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 4-methoxy-benzyl ester

Conditions	Yield
In N,N-dimethyl-formamide

Upstream product

• 1672-50-0 4,5-diamino-6-hydroxypyrimidine 
• 4316-94-3 6-chloro-5-nitropyrimidin-4-amine 

Downstream Products

• 1126-23-4 8-methyl-1,7-dihydro-purine-6-thione 
• 65882-61-3 3H-pteridine-4-thione 
• 195141-69-6 6-benzylsulfanyl-pyrimidine-4,5-diamine 
• 6223-63-8 8-amino-1,7-dihydro-purine-6-thione 
• 24079-37-6 Dithiopurine 
• 20917-46-8 6-Thioxopurin-8-on 
• 2846-90-4 [1,3]thiazolo[5,4-d]pyrimidin-7-amine 
• 6306-88-3 7-Anilino-<1,2,5>thiadiazolo<3,4-d>pyrimidin 
• 363618-27-3 2-(5,6-diamino-pyrimidin-4-ylsulfanyl)-5-nitro-benzonitrile 
• 89797-62-6 7-Thioxo-<1.2.5>thiadiazolo<3,4-d>pyrimidin-(6H) 
• 21323-67-1 7-Amino-<1,2,3>thiadiazolo<5,4-d>pyrimidin 
• 55383-58-9 4,6-Diaminopyrimido<4,5-b>-1,4-thiazin 
• 6223-69-4 2,4-Diamino-thiazolo<5,4-d>pyrimidin 

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