ChemicalBook--->CAS DataBase List--->890094-38-9

890094-38-9

890094-38-9 Structure

890094-38-9 Structure
IdentificationBack Directory
[Name]

(2-chloro-5-nitro-pyrimidin-4-yl)-isopropyl-amine
[CAS]

890094-38-9
[Synonyms]

2-Chloro-N-isopropyl-5-nitropyrimidin-4-amine
2-chloro-5-nitro-N-propan-2-ylpyrimidin-4-amine
(2-chloro-5-nitro-pyrimidin-4-yl)-isopropyl-amine
4-Pyrimidinamine, 2-chloro-N-(1-methylethyl)-5-nitro-
[Molecular Formula]

C7H9ClN4O2
[MDL Number]

MFCD07440214
[MOL File]

890094-38-9.mol
[Molecular Weight]

216.62
Chemical PropertiesBack Directory
[Boiling point ]

407.0±30.0 °C(Predicted)
[density ]

1.420±0.06 g/cm3(Predicted)
[storage temp. ]

under inert gas (nitrogen or Argon) at 2-8°C
[pka]

-0.65±0.10(Predicted)
[Appearance]

Light yellow to yellow Solid
[InChI]

InChI=1S/C7H9ClN4O2/c1-4(2)10-6-5(12(13)14)3-9-7(8)11-6/h3-4H,1-2H3,(H,9,10,11)
[InChIKey]

XGDPRAOPHIPUTB-UHFFFAOYSA-N
[SMILES]

C1(Cl)=NC=C([N+]([O-])=O)C(NC(C)C)=N1
Spectrum DetailBack Directory
[Spectrum Detail]

(2-chloro-5-nitro-pyrimidin-4-yl)-isopropyl-amine(890094-38-9)1HNMR
Hazard InformationBack Directory
[Synthesis]

Isopropylamine

75-31-0

2,4-Dichloro-5-nitropyrimidine

49845-33-2

(2-chloro-5-nitro-pyrimidin-4-yl)-isopropyl-amine

890094-38-9

A mixed solution was prepared by dissolving isopropylamine (4.5 mL) and N,N-diisopropylethylamine (13.2 mL) in 150 mL of dichloromethane. The mixed solution was slowly added dropwise to a solution of dichloromethane (30 mL) containing 2,4-dichloro-5-nitropyrimidine (10.0 g) at 0 °C. After the dropwise addition was completed, the reaction mixture was kept at 0 °C to continue the reaction for 30 min. After completion of the reaction, the product was purified by column chromatography to afford the bright yellow solid product 2-chloro-N-isopropyl-5-nitropyrimidin-4-amine (10.1 g) in 90.4% yield. The product was characterized by 1H NMR (400 MHz, CDCl3): δ 9.03 (s, 1H), 8.24 (s, 1H), 4.53 (m, 1H), 1.34 (d, J = 6.8 Hz, 6H) ppm.

[References]

[1] Journal of Medicinal Chemistry, 2012, vol. 55, # 23, p. 10685 - 10699
[2] Patent: EP2578584, 2013, A1. Location in patent: Paragraph 0075; 0076
[3] Patent: WO2011/101369, 2011, A1. Location in patent: Page/Page column 48
[4] Patent: US2012/329803, 2012, A1. Location in patent: Page/Page column 20
[5] Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 16, p. 4360 - 4365
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