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

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

9synthesis methods

Product Name:4-Chloro-5-iodo-7H-pyrrol[2,3-d]pyrimidine
CAS Number:123148-78-7
Molecular formula:C6H3ClIN3
Molecular Weight:279.47

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

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

3680-69-1 Synthesis

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

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

123148-78-7
258 suppliers
$8.00/1g

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%;T_m212-214° C. (dec);UV λ_max: 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

FullText

3680-69-1 Synthesis

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

123148-78-7
258 suppliers
$8.00/1g

References

3680-71-5 Synthesis