ChemicalBook--->CAS DataBase List--->815610-16-3

815610-16-3

815610-16-3 Structure

815610-16-3 Structure
IdentificationBack Directory
[Name]

4-Iodopyrimidin-2-amine
[CAS]

815610-16-3
[Synonyms]

4-Iodopyrimidin-2-amine
2-Amino-4-iodopyrimidine
2-Pyrimidinamine, 4-iodo-
4-Iodo-pyrimidin-2-ylamine
4-Iodopyrimidin-2-amine ISO 9001:2015 REACH
[Molecular Formula]

C4H4IN3
[MDL Number]

MFCD12406140
[MOL File]

815610-16-3.mol
[Molecular Weight]

221
Chemical PropertiesBack Directory
[Boiling point ]

364.9±34.0 °C(Predicted)
[density ]

2.204±0.06 g/cm3(Predicted)
[storage temp. ]

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

3.27±0.10(Predicted)
[Appearance]

Off-white to light brown Solid
Safety DataBack Directory
[Symbol(GHS) ]

Exclamation Mark (GHS07)
GHS07
[Signal word ]

Warning
[Hazard statements ]

H302-H315-H319-H332-H335
[Precautionary statements ]

P261-P280-P305+P351+P338
Spectrum DetailBack Directory
[Spectrum Detail]

4-Iodopyrimidin-2-amine(815610-16-3)1HNMR
Hazard InformationBack Directory
[Synthesis]

2-Amino-4-chloropyrimidine

3993-78-0

4-Iodopyrimidin-2-amine

815610-16-3

The general procedure for the synthesis of 2-amino-4-iodopyrimidine using 2-amino-4-chloropyrimidine as starting material was as follows: 2-amino-4-chloropyrimidine (13.0 g, 100 mmol) was slowly added to 57 wt% aqueous hydriodic acid solution (115 mL, 1.00 mol) at 0 °C. The reaction mixture was stirred continuously for 3 hours at room temperature. Subsequently, the mixture was cooled to 0 °C and the resulting precipitate was removed by filtration. The filter cake was transferred to a pre-cooled aqueous 5 N Na2CO3 solution (200 mL). The aqueous phase was extracted using ethyl acetate (3 × 500 mL), and the combined organic phases were concentrated under reduced pressure to afford 2-amino-4-iodopyrimidine (21.1 g, 95.0 mmol, 95% yield) as a white solid. The product was characterized by 1H NMR (400 MHz, DMSO-d6): δ 7.78 (d, J = 5.0 Hz, 1H), 7.02 (br.s, 2H), 7.00 (d, J = 5.0 Hz, 1H). The mass spectrum (ESI, cation mode) showed m/z: 222.1 ([M + H]+).

[References]

[1] European Journal of Medicinal Chemistry, 2014, vol. 80, p. 364 - 382
[2] Organic Letters, 2014, vol. 16, # 3, p. 708 - 711
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