ChemicalBook CAS DataBase List 5-Bromo-2-iodopyrimidine

5-Bromo-2-iodopyrimidine synthesis

4synthesis methods

Product Name:5-Bromo-2-iodopyrimidine
CAS Number:183438-24-6
Molecular formula:C4H2BrIN2
Molecular Weight:284.88

5-Bromo-2-iodopyrimidine was used to prepare novel conformationally constrained glucagon receptor antagonists. It can be synthesized by iodination of 5-bromo-2-chloro-pyrimidine, sodium iodide and Hydroiodic acid.

32779-36-5 Synthesis

32779-36-5
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$5.00/5g

183438-24-6
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$6.00/1g

Yield:183438-24-6 84%

Reaction Conditions:

Stage #1:5-Bromo-2-chloropyrimidine with hydrogen iodide;sodium iodide in chloroform;water at 0 - 20; for 20 h;
Stage #2: with sodium hydroxide in chloroform;water for 0.166667 h;

Steps:

A Preparation of 5-Bromo-2-iodo-pyrimidine
Preparation of 5-Bromo-2-iodo-pyrimidine To a suspension of 5-bromo-2-chloro-pyrimidine (5.80 g, 30 mmol) and sodium iodide (7.5 g, 50 mmol) in chloroform (20 ml) a Hydroiodic acid (57 wt. %) (2.85 g, 25.6 mmol) is added at 0° C. After removing the cooling the reaction mixture is stirred for 20 h at r.t. and then poured into a mixture of 200 ml ice water and 30 ml 10N NaOH. Chloroform (150 ml) is added and the mixture is stirred for 10 min. The organic phase is separated, the aqueous layer is extracted with chloroform (2*100 ml) and the combined organic phases dried over MgSO₄ and concentrated in vacuo to yielding 5-bromo-2-iodo-pyrimidine as a pale yellow solid. Yield 6.29 g (84%) MS: M=284.8 (ESI+) ¹H-NMR (300 MHz, CDCl3): 8.54 (s, 2H) 7.56(d, J=16.4 Hz, 1H), 7.59-7.66(m, 4H).

References:

Bossenmaier, Birgit;Friebe, Walter-Gunar;Jenni, Wolfgang;Rueth, Matthias;Voss, Edgar US2005/222228, 2005, A1 Location in patent:Page/Page column 15-16

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7752-82-1 Synthesis