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ChemicalBook CAS DataBase List 4-Chloro-5-iodo-7H-pyrrol[2,3-d]pyrimidine
123148-78-7

4-Chloro-5-iodo-7H-pyrrol[2,3-d]pyrimidine synthesis

9synthesis methods
4-chloro-7h-pyrrole [2,3-d] pyrimidine (8.0 g, 52.32 mmol, 1.0 eq) was dissolved in DMF(40 mL) and NIS(15.7g, 57.55 mmol, 1.1eq) was added at 0℃. After stirring at room temperature overnight, 200 mL of saturated Na2S2O3 solution was added. The mixture was filtered, washed with water three times, and vacuum drying, to obtain 4-Chloro-5-iodo-7H-pyrrol[2,3-d]pyrimidine.
516-12-1 Synthesis
N-Iodosuccinimide

516-12-1
541 suppliers
$5.00/5g

3680-69-1 Synthesis
4-Chloro-7H-pyrrolo[2,3-d]pyrimidine

3680-69-1
827 suppliers
$6.00/1g

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Yield:123148-78-7 86.9%

Reaction Conditions:

in N,N-dimethyl-formamide at 20;

Steps:

1.1
Step 1:4-Chloro-7H-pyrrolo[2,3-d]pyrimidine 10.75 g (70 mmol) and N-iodosuccinimide (16.8 g, 75 mmol) were dissolved in 400 mL of dry DMF and left at ambient temperature in the darkness over night. The solvent was evaporated. The yellow residue was suspended in hot 10% solution of Na2SO3, filtered, washed twice with hot water and crystallized from ethanol to yield 14.6 g (74.6%) of the title compound as off-white crystals. The mother liquid was evaporated up to volume and crystallized again from ethanol to give 2.47 g (12.3%) of the target compound. The total yield is close to 100%;Tm 212-214° C. (dec);UV λmax: 307, 266, 230, 227 nm (methanol);MS: 277.93 (M-H), 313 (M+Cl);1H-NMR (DMSO-d6): 12.94 (s, 1H, NH), 8.58 (s, 1H), 7.94 (s, 1H).

References:

Genelabs Technologies, Inc.;Gilead Sciences, Inc. US2009/48189, 2009, A1 Location in patent:Page/Page column 36

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