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Sigma-Aldrich

5-Amino-4,6-dichloropyrimidine

97%

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About This Item

Fórmula empírica (Notação de Hill):
C4H3Cl2N3
Número CAS:
5413-85-4
Peso molecular:
163.99
Beilstein:
126885
Número CE:
226-503-7
Número MDL:
MFCD00006108
Código UNSPSC:
12352100
ID de substância PubChem:
24853030
NACRES:
NA.22

Ensaio

97%

forma

liquid

pf

145-148 °C (lit.)

solubilidade

95% ethanol: soluble 50 mg/mL, clear to slightly hazy, colorless to faintly yellow

temperatura de armazenamento

2-8°C

cadeia de caracteres SMILES

Nc1c(Cl)ncnc1Cl

InChI

1S/C4H3Cl2N3/c5-3-2(7)4(6)9-1-8-3/h1H,7H2

chave InChI

NIGDWBHWHVHOAD-UHFFFAOYSA-N

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Aplicação

5-Amino-4,6-dichloropyrimidine was used in the synthesis of:
  • oxepane ring containing monocyclic, conformationally restricted bicyclic and spirocyclic nucleosides
  • conformationally locked bicyclo[2.2.1]heptane/oxa-bicyclo[3.2.1]octane nucleosides
  • N(7)-substituted purines
  • chiral derivatives of (+)-erythro-9-(2-hydroxy-3-nonyl)adenine
  • 9-alkyl-6-substituted-purine analogs, potent anticonvulsant agents
  • pyrimido-oxazepines in a three-step process with microwave heating at 150°C

Pictogramas

Exclamation mark
GHS07

Palavra indicadora

Warning

Frases de perigo

H315,H319,H335

Classificações de perigo

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Órgãos-alvo

Respiratory system

Código de classe de armazenamento

11 - Combustible Solids

Classe de risco de água (WGK)

WGK 3

Ponto de fulgor (°F)

Not applicable

Ponto de fulgor (°C)

Not applicable

Equipamento de proteção individual

dust mask type N95 (US), Eyeshields, Gloves

Certificados de análise (COA)

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J L Kelley et al.
Journal of medicinal chemistry, 31(3), 606-612 (1988-03-01)
Several 9-alkyl-6-substituted-purines were synthesized and tested for anticonvulsant activity against maximal electroshock-induced seizures (MES) in rats. Most compounds were prepared in three steps from 5-amino-4,6-dichloropyrimidine or in two steps via alkylation of 6-chloropurine. Potent anticonvulsant activity against MES resided in
Jinglin Liu et al.
Journal of combinatorial chemistry, 8(3), 410-416 (2006-05-09)
A regiospecific strategy for the preparation of N(7)-substituted purines in an efficient manner was devised. This approach to 6,7,8-trisubstituted purines relies on the cyclization reactions of suitably substituted pyrimidines (1) with either a carboxylic acid or an aldehyde. The method
Subhankar Tripathi et al.
The Journal of organic chemistry, 72(19), 7427-7430 (2007-08-25)
Carbohydrate-derived substrates having (i) C-5 nitrone and C-3-O-allyl, (ii) C-4 vinyl and a C-3-O-tethered nitrone, and (iii) C-5 nitrone and C-4-allyloxymethyl generated tetracyclic isoxazolidinooxepane/-pyran ring systems upon intramolecular nitrone cycloaddition reactions. Deprotection of the 1,2-acetonides of these derivatives followed by
G C Harriman et al.
Journal of medicinal chemistry, 35(22), 4180-4184 (1992-10-30)
The synthesis of various chiral derivatives of (+)-erythro-9-(2-hydroxy-3-nonyl)adenine, (+)-EHNA, from (2S,3R)-3-amino-1,2-O-isopropylidene-1,2-nonanediol by condensation with 5-amino-4,6-dichloropyrimidine is described. The compounds synthesized were C1'- and nor-C1'-(+)-EHNA derivatives. When tested with calf spleen ADA, C1'-OH- and nor-C1'-(+)-EHNA had comparable inhibitory activity that was
Sk Sahabuddin et al.
The Journal of organic chemistry, 71(16), 5980-5992 (2006-07-29)
The carbohydrate-derived substrate 3-C-allyl-1,2:5,6-di-O-isopropylidene-alpha-D-allofuranose was judiciously manipulated for preparing suitable synthons, which could be converted to a variety of isoxazolidino-spirocycles and -tricycles through the application of ring-closing metathesis (RCM) and intramolecular nitrone cycloaddition (INC) reactions. Cleavage of the isoxazolidine rings
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