N-(2-Amino-4,6-Dichloro-5-Pyrimidinyl)Formamide supplier

Name
N-(2-Amino-4,6-dichloro-5-pyrimidinyl)formamide
EINECS 425-650-6
CAS No. 171887-03-9
Article Data9
CAS DataBase
Density 1.742 g/cm³
Solubility
Melting Point 4.5 °C
Formula C₅H₄Cl₂N₄O
Boiling Point 554.77 °C at 760 mmHg
Molecular Weight 207.019
Flash Point 289.315 °C
Transport Information
Appearance
Safety
Risk Codes R36/38; R36/37/38
Molecular Structure
Hazard Symbols Xi
Synonyms N-(2-Amino-4,6-dichloropyrimidin-5-yl)formamide;N-(2-Amino-4,6-dichloro-5-pyrimidinyl)formamide;
PSA 80.90000
LogP 2.22400

Synthetic route

: 2-nitroso-4,6-dichloro-5-formamidopyrimidine

: 171887-03-9
N-(2-amino-4,6-dichloropyrimidin-5-yl)formamide

Conditions

Conditions	Yield
With 5%-palladium/activated carbon; hydrogen In methanol at 40℃; under 7500.75 - 11251.1 Torr; for 4h; Temperature; Autoclave;	98%

: 64-18-6
formic acid

: 55583-59-0
2,5-diamino-4,6-dichloropyrimidine

: 171887-03-9
N-(2-amino-4,6-dichloropyrimidin-5-yl)formamide

Conditions

Conditions	Yield
Stage #1: formic acid; 2,5-diamino-4,6-dichloropyrimidine at 50 - 55℃; for 3h; Stage #2: In toluene at 50℃; under reduced pressure;	90%

: 2,5-diamino-4,6-dihydroxypyrimidine hydrochloride

: 68-12-2, 33513-42-7
N,N-dimethyl-formamide

: 171887-03-9
N-(2-amino-4,6-dichloropyrimidin-5-yl)formamide

Conditions

Conditions	Yield
With thionyl chloride; trichlorophosphate at 80℃; for 2.5h; Temperature;	82.6%

: 171887-02-8
2-amino-5-{[(dimethylamino)methylene]amino}-4,6-dichloropyrimidine

: 171887-03-9
N-(2-amino-4,6-dichloropyrimidin-5-yl)formamide

Conditions

Conditions	Yield
In phosphate buffer for 4h; pH=3.2; Hydrolysis; Heating;	72%

: 2-Amino-4,6-dichloro-5-[(dimethylamino)methyleneamino]pyrimidine

: 171887-03-9
N-(2-amino-4,6-dichloropyrimidin-5-yl)formamide

Conditions

Conditions	Yield
With potassium dihydrogenphosphate; phosphoric acid In chloroform methanol	68%

: 56830-58-1
2,5-Diamino-4,6-dihydroxypyrimidine hydrochloride

: 68-12-2, 33513-42-7
N,N-dimethyl-formamide

: 171887-03-9
N-(2-amino-4,6-dichloropyrimidin-5-yl)formamide

Conditions

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%

: 4,6-Dichloro-2,5-bis-[(dimethylamino)methyleneamino]pyrimidine

: 56830-58-1
2,5-Diamino-4,6-dihydroxypyrimidine hydrochloride

: 171887-03-9
N-(2-amino-4,6-dichloropyrimidin-5-yl)formamide

Conditions

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

: 56830-58-1
2,5-Diamino-4,6-dihydroxypyrimidine hydrochloride

: 171887-03-9
N-(2-amino-4,6-dichloropyrimidin-5-yl)formamide

Conditions

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

: 171887-01-7
2,5-bis{[(dimethylamino)methylene]amino}-4,6-dichloropyrimidine

: 171887-03-9
N-(2-amino-4,6-dichloropyrimidin-5-yl)formamide

Conditions

Conditions	Yield
With sodium hydroxide; phosphoric acid; water at 100℃; for 4h; pH=4; Product distribution / selectivity;

: 55583-59-0
2,5-diamino-4,6-dichloropyrimidine

: 171887-03-9
N-(2-amino-4,6-dichloropyrimidin-5-yl)formamide

Conditions

Conditions	Yield
With formic acid In water; toluene

: 171887-03-9
N-(2-amino-4,6-dichloropyrimidin-5-yl)formamide

: 57260-71-6
1-t-Butoxycarbonylpiperazine

: 1435953-79-9
4-[2-amino-6-chloro-5-(formylamino)pyrimidin-4-yl]piperazine-1-carboxylic acid tert-butyl ester

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In 1,4-dioxane at 55℃; for 1h;	100%
With N-ethyl-N,N-diisopropylamine In 1,4-dioxane at 55℃; for 1h;	100%
With N-ethyl-N,N-diisopropylamine In 1,4-dioxane at 55℃; for 1h;	100%

: 171887-03-9
N-(2-amino-4,6-dichloropyrimidin-5-yl)formamide

: 1211527-74-0
7-chlorothiazolo[5,4-d]pyrimidin-5-amine

Conditions

Conditions	Yield
With Lawessons reagent In tetrahydrofuran at 65℃; for 0.5h;	93.4%
With Lawessons reagent In tetrahydrofuran at 65℃; for 0.5h;	93.4%
With Lawessons reagent In tetrahydrofuran at 65℃; for 0.5h;	93.4%

: 1037397-91-3
(3-methyl-4-nitrophenyl)methanamine hydrochloride

: 171887-03-9
N-(2-amino-4,6-dichloropyrimidin-5-yl)formamide

: 1040353-71-6
N-[2-amino-4-chloro-6-(3-methyl-4-nitro-benzylamino)-pyrimidin-5-yl]-formamide

Conditions

Conditions	Yield
With triethylamine In isopropyl alcohol at 58 - 65℃; for 3.5 - 4.66667h; Heating / reflux;	92%

: ((1S,4R)-4-aminocyclopent-2-enyl)methanol D-hydrogen tartrate

: 171887-03-9
N-(2-amino-4,6-dichloropyrimidin-5-yl)formamide

: 171887-04-0
(1R,4S)-1-[(2-amino-6-chloro-5-formamido-4-pyrimidinyl)amino]-4-(hydroxymethyl)-2-cyclopentene

Conditions

Conditions	Yield
Stage #1: ((1S,4R)-4-aminocyclopent-2-enyl)methanol D-hydrogen tartrate With sodium carbonate In isopropyl alcohol at 20℃; for 1h; Stage #2: N-(2-amino-4,6-dichloropyrimidin-5-yl)formamide In isopropyl alcohol Concentration; Solvent; Reflux;	88.2%

: (1S,2R,3S,4R,5R)-4-[((1,1-dimethylethyl)dimethylsilyloxy)]-5-[((1,1-dimethylethyl)dimethyl-silyloxy)methyl]-3-fluorobicyclo[3.1.0]hexan-2-amine

: 171887-03-9
N-(2-amino-4,6-dichloropyrimidin-5-yl)formamide

: C24H43ClFN5O3Si2

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In 1,4-dioxane at 100℃; for 12h; Microwave irradiation;	88%
With N-ethyl-N,N-diisopropylamine In 1,4-dioxane at 100℃; for 12h; Microwave irradiation;	88%

: 136522-35-5
(1R,4S)-1-amino-4-hydroxymethyl-2-cyclopentene

: 171887-03-9
N-(2-amino-4,6-dichloropyrimidin-5-yl)formamide

: 171887-04-0
(1R,4S)-1-[(2-amino-6-chloro-5-formamido-4-pyrimidinyl)amino]-4-(hydroxymethyl)-2-cyclopentene

Conditions

Conditions	Yield
With triethylamine In ethanol; water	85%
With triethylamine In ethanol for 7h; Substitution; Heating;	83%
With sodium hydroxide; triethylamine In acetic acid 1-hydroxy-propyl ester; ethanol
Stage #1: (1R,4S)-1-amino-4-hydroxymethyl-2-cyclopentene; N-(2-amino-4,6-dichloropyrimidin-5-yl)formamide With triethylamine In industrial methylated spirit; water for 17h; Heating / reflux; Stage #2: With potassium carbonate In industrial methylated spirit at 25 - 30℃; for 0.5h; Stage #3: In industrial methylated spirit at 0 - 5℃; Product distribution / selectivity;
Stage #1: (1R,4S)-1-amino-4-hydroxymethyl-2-cyclopentene; N-(2-amino-4,6-dichloropyrimidin-5-yl)formamide With sodium hydrogencarbonate In idustrial methylated spirit; water for 4h; Heating / reflux; Stage #2: In industrial methylated spirit at -5℃; for 1h; Product distribution / selectivity;

: ((1R*,3R*,4R*)-3-aminobicyclo[2.2.1]heptan-1-yl)methanol

: 171887-03-9
N-(2-amino-4,6-dichloropyrimidin-5-yl)formamide

: [(1R*,3R*,4R*)-3-(2-amino-6-chloro-9H-purin-9-yl)bicyclo[2.2.1]hept-1-yl]methanol

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In ethanol; water at 140℃; for 1h; Microwave irradiation; Sealed tube;	83%

: (4-aminobicyclo[2.2.1]hept-1-yl)methanol

: 171887-03-9
N-(2-amino-4,6-dichloropyrimidin-5-yl)formamide

: [4-(2-amino-6-chloro-9H-purin-9-yl)bicyclo[2.2.1]hept-1-yl]methanol

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In butan-1-ol at 160℃; for 2h; Sealed tube; Microwave irradiation;	81%

: 2835-68-9
4-aminobenzamide

: 171887-03-9
N-(2-amino-4,6-dichloropyrimidin-5-yl)formamide

: 4-(2-amino-6-((4-carbamoylphenyl)amino)9H-purin-9-yl)benzamide

Conditions

Conditions	Yield
In 1,4-dioxane; water Reflux;	79%

: 171887-03-9
N-(2-amino-4,6-dichloropyrimidin-5-yl)formamide

: 55583-59-0
2,5-diamino-4,6-dichloropyrimidine

Conditions

Conditions	Yield
With hydrogenchloride In ethanol; water for 6h; Hydrolysis; Heating;	77%
In hydrogenchloride; ethanol	65%

: ((1R,2R,3S,4R)-4-amino-2,3-bis((tert-butyldimethylsilyl)oxy)cyclopentyl)methanol

: 171887-03-9
N-(2-amino-4,6-dichloropyrimidin-5-yl)formamide

: ((1R,2R,3S,4R)-4-(2-amino-6-chloro-9H-purin-9-yl)-2,3-bis((tert-butyldimethylsilyl)oxy)cyclopentyl)methanol

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In butan-1-ol at 160℃; for 24h; Sealed tube;	75%
With N-ethyl-N,N-diisopropylamine; butan-1-ol at 160℃; for 24h; Sealed tube;	75%
With N-ethyl-N,N-diisopropylamine In butan-1-ol at 160℃; for 24h; Sealed tube;

: (1R,4S)-1-amino-4-(hydroxymethyl)-2-cyclopentene hydrochloride

: 171887-03-9
N-(2-amino-4,6-dichloropyrimidin-5-yl)formamide

: 171887-04-0
(1R,4S)-1-[(2-amino-6-chloro-5-formamido-4-pyrimidinyl)amino]-4-(hydroxymethyl)-2-cyclopentene

Conditions

Conditions	Yield
With sodium hydroxide; triethylamine In 2-methyl-propan-1-ol	74%
Stage #1: (1R,4S)-1-amino-4-(hydroxymethyl)-2-cyclopentene hydrochloride With sodium hydrogencarbonate In isopropyl alcohol at 20℃; for 1h; Stage #2: N-(2-amino-4,6-dichloropyrimidin-5-yl)formamide In isopropyl alcohol Concentration; Reagent/catalyst; Reflux;	51.4%
Stage #1: (1R,4S)-1-amino-4-(hydroxymethyl)-2-cyclopentene hydrochloride With sodium hydrogencarbonate In ethanol at 20℃; for 0.5h; Inert atmosphere; Stage #2: N-(2-amino-4,6-dichloropyrimidin-5-yl)formamide In ethanol at 75 - 80℃; for 3h; Inert atmosphere;

: 1202402-79-6
(S)-(6-(((tetrahyd rofuran-3-yl)oxy)methyl)pyridin-2-yl)methanamine

: 171887-03-9
N-(2-amino-4,6-dichloropyrimidin-5-yl)formamide

: 1202402-77-4
N-[2-amino-4-chloro-6-((6-[(S)-(tetrahydro-furan-3-yl)oxymethyl]pyridin-2-ylmethyl)amino)pyrimidin-5-yl]formamide

Conditions

Conditions	Yield
With triethylamine In isopropyl alcohol for 2h; Reflux;	73%

: (±)-cis-3-aminocyclopentanol

: 171887-03-9
N-(2-amino-4,6-dichloropyrimidin-5-yl)formamide

: 2-amino-6-chloro-9-(cis-3′-hydroxycyclopentyl)purine

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In ethanol; water at 140℃; for 1.5h; Microwave irradiation; Sealed tube;	72%

: (1S,2R,3S,4R,5R)-4-[((1,1-dimethylethyl)dimethylsilyloxy)]-5-[((1,1-dimethylethyl)dimethyl-silyloxy)methyl]-3-fluorobicyclo[3.1.0]hexan-2-amine

: 171887-03-9
N-(2-amino-4,6-dichloropyrimidin-5-yl)formamide

A: C24H43ClFN5O3Si2

B: C24H41ClFN5O2Si2

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In toluene at 160℃; for 2h; Microwave irradiation;	A 70% B 24%
With N-ethyl-N,N-diisopropylamine In butan-1-ol at 160℃; for 2h; Solvent; Microwave irradiation;	A 59% B 40%

...Expand

: 155899-66-4
(3aR,4S,6R,6aS)-6-amino-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-ol

: 171887-03-9
N-(2-amino-4,6-dichloropyrimidin-5-yl)formamide

: 9-[(1′R,2′S,3′R,4′S)-4′-hydroxy-2′,3′-O-isopropylidene-cyclopentan-1′-yl]-2-amino-6-chloro-9H-purine

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In butan-1-ol at 120℃;	66%

: (1SR,2SR,4SR)-4-aminobicyclo[2.2.1]heptan-2-ol hydrochloride

: 171887-03-9
N-(2-amino-4,6-dichloropyrimidin-5-yl)formamide

: 4-(2-amino-6-chloro-9H-purin-9-yl)bicyclo[2.2.1]heptan-2-ol

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In butan-1-ol at 160℃; for 2h; Microwave irradiation;	63%

: C7H11N

: 171887-03-9
N-(2-amino-4,6-dichloropyrimidin-5-yl)formamide

: 1621165-38-5
C12H12ClN5

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In butan-1-ol at 160℃; for 2h; Sealed tube; Microwave irradiation;	57%

: 4-pentylbicyclo[2.2.2]oct-1-ylamine

: 171887-03-9
N-(2-amino-4,6-dichloropyrimidin-5-yl)formamide

: 1621165-41-0
C18H26ClN5

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In butan-1-ol at 160℃; for 2h; Sealed tube; Microwave irradiation;	57%

: 171887-03-9
N-(2-amino-4,6-dichloropyrimidin-5-yl)formamide

: 90597-13-0
(3aS,4R,6R,6aR)-6-((methoxymethoxy)methyl)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-amine

: 1203452-14-5
(1R,2S,3R,4R)-1-[(2-amino-6-chloro-5-formamido-4-pyrimidinyl)amino]-2,3-isopropylidenedioxy-4-(methoxymethoxymethyl)cyclopentane

Conditions

Conditions	Yield
With triethylamine In ethanol for 7h; Reflux;	51.5%

: (4R,3R,1R)-4-amino-3-hydroxy-1-trityloxymethylphospholane 1-oxide

: 171887-03-9
N-(2-amino-4,6-dichloropyrimidin-5-yl)formamide

: (4R,3R,1R)-4-(guanin-9-yl)-3-hydroxy-1-hydroxymethylphospholane 1-oxide

Conditions

Conditions	Yield
Stage #1: (4R,3R,1R)-4-amino-3-hydroxy-1-trityloxymethylphospholane 1-oxide; N-(2-amino-4,6-dichloropyrimidin-5-yl)formamide With N-ethyl-N,N-diisopropylamine In butan-1-ol at 130℃; for 16h; Stage #2: With hydrogenchloride In methanol at 60℃; for 16h;	48%

: 1202403-02-8
2-(6-(aminomethyl)pyridin-2-yl)propan-2-ol

: 171887-03-9
N-(2-amino-4,6-dichloropyrimidin-5-yl)formamide

: 1202402-84-3
7-chloro-3-(6-[1-hydroxy-1-methylethyl]pyridine-2-ylmethyl)-3H-[1,2,3]triazolo[4,5-d]pyrimidin-5-amine

Conditions

Conditions	Yield
Stage #1: 2-(6-(aminomethyl)pyridin-2-yl)propan-2-ol; N-(2-amino-4,6-dichloropyrimidin-5-yl)formamide With triethylamine In isopropyl alcohol at 90℃; for 4h; Stage #2: With hydrogenchloride In ethanol; water at 90℃; for 2h; Stage #3: With sodium nitrite In ethanol; water at 0℃;	47%

: (4S,3S,1R)-4-amino-3-hydroxy-1-trityloxymethylphospholane 1-oxide

: 171887-03-9
N-(2-amino-4,6-dichloropyrimidin-5-yl)formamide

: (4S,3S,1R)-4-(guanin-9-yl)-3-hydroxy-1-hydroxymethylphospholane 1-oxide

Conditions

Conditions	Yield
Stage #1: (4S,3S,1R)-4-amino-3-hydroxy-1-trityloxymethylphospholane 1-oxide; N-(2-amino-4,6-dichloropyrimidin-5-yl)formamide With N-ethyl-N,N-diisopropylamine In butan-1-ol at 130℃; for 16h; Stage #2: With hydrogenchloride In methanol at 60℃; for 16h;	45%

: 886766-31-0
tert-butyl 5,8-diazaspiro[3.5]nonane-8-carboxylate

: 171887-03-9
N-(2-amino-4,6-dichloropyrimidin-5-yl)formamide

: 1435953-91-5
tert-butyl 9-(2-amino-6-chloro-5-formamidopyrimidin-4-yl)-6,9-diazaspiro[3.5]-nonane-6-carboxylate

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In dichloromethane for 20h;	22%
With N-ethyl-N,N-diisopropylamine In 1,4-dioxane at 100℃; for 168h;	0.44 g

N-(2-Amino-4,6-Dichloro-5-Pyrimidinyl)Formamide Specification

The N-(2-Amino-4,6-Dichloro-5-Pyrimidinyl)Formamide, with the CAS registry number 171887-03-9, is also known as N-(2-Amino-4,6-dichloropyrimidin-5-yl)formamide; 2-Amino-4,6-dichloro-5-formamidopyrimidine. It belongs to the product categories of Bases & Related Reagents;Heterocycles;Nucleotides.This chemical's molecular formula is C5H4Cl2N4O and molecular weight is 207.02. What's more,Its systematic name is N-(2-Amino-4,6-Dichloro-5-Pyrimidinyl)Formamide.It is an Abacavir intermediate,A purine derivative.

Physical properties about N-(2-Amino-4,6-Dichloro-5-Pyrimidinyl)Formamide are:
(1)ACD/LogP: 1.202; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.20; (4)ACD/LogD (pH 7.4): 1.20; (5)ACD/BCF (pH 5.5): 4.83; (6)ACD/BCF (pH 7.4): 4.83; (7)ACD/KOC (pH 5.5): 107.40; (8)ACD/KOC (pH 7.4): 107.39; (9)#H bond acceptors: 5; (10)#H bond donors: 3; (11)#Freely Rotating Bonds: 1; (12)Index of Refraction: 1.706; (13)Molar Refractivity: 46.258 cm³; (14)Molar Volume: 118.837 cm³; (15)Surface Tension: 85.0719985961914 dyne/cm; (16)Density: 1.742 g/cm³; (17)Flash Point: 289.315 °C; (18)Enthalpy of Vaporization: 83.592 kJ/mol; (19)Boiling Point: 554.77 °C at 760 mmHg; (20)Vapour Pressure: 0 mmHg at 25°C.

You can still convert the following datas into molecular structure:
(1)SMILES:Clc1nc(nc(Cl)c1NC=O)N;
(2)Std. InChI:InChI=1S/C5H4Cl2N4O/c6-3-2(9-1-12)4(7)11-5(8)10-3/h1H,(H,9,12)(H2,8,10,11);
(3)Std. InChIKey:XYWHZUCZNRMJGO-UHFFFAOYSA-N.

Product Name

N-(2-Amino-4,6-dichloro-5-pyrimidinyl)formamide

Synthetic route

N-(2-Amino-4,6-Dichloro-5-Pyrimidinyl)Formamide Specification

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