Cladribine synthesis

5synthesis methods

Product Name:Cladribine
CAS Number:4291-63-8
Molecular formula:C10H12ClN5O3
Molecular Weight:285.69

2,6-Dichloropurine and sodium hydride in acetonitrile were stirred at room temperature for 30 min under nitrogen protection. 1-Chloro-2-deoxy-3,5-di-O-p-toluoyl-α-D-erythro-pentofuranose was added in batches within 20 min with stirring, and stirred for 15 h. A small amount of insoluble matter was filtered off, and the filtrate was concentrated. The remaining oily substance was purified by silica gel column chromatography (toluene-acetone/9:1) to obtain solid compound (I) in a yield of 59%. Compound (I) was dissolved in 60 ml of saturated ammonia methanol solution (saturated at 0°C), and stirred at 100°C for 5 h. The reaction solution was evaporated to dryness, and the residue was purified by silica gel column chromatography (chloroform-methanol/8:2) to obtain cladribine.

Adenosine, 2-chloro-2'-deoxy-, 3',5'-diacetate

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Yield:4291-63-8 93%

Reaction Conditions:

with sodium carbonate in methanol; pH=8 - 9 at 20; for 2 h;

Steps:

Cladribine (2)
Compounde 7 (0.074 g, 0.20 mmol) was dissolved in MeOH (2 mL) andthe pH value was adjusted to 8-9 with Na2CO3. The mixture was stirred atroom temperature for 2 hours and concentrated under reduced pressure.The crude product was purified by flash column chromatography on silicagel using CHCl3/MeOH (1/1) as eluent to give 2, yield 93%.White solid, m.p. 306-310°C (dec.). 1H NMR (400 MHz, DMSO-d6): δ8.34 (s, 1H), 7.34 (brs, 2H), 6.36-6.33 (m, 1H), 5.34 (s, 1H), 5.29 (s, 1H),4.11 (t, J = 2.4 Hz, 1H), 3.90-3.87 (m, 1H), 3.64 (dd, J 1 = 11.6 Hz, J 2 =39.2 Hz, 2H), 2.76-2.69 (m, 1H), 2.28-2.21 (m, 1H); 13C NMR (100 MHz, DMSO-d6) δ 155.9, 153.7, 148.7, 139.4, 119.0, 87.8, 83.8, 70.8, 61.7, 42.0;HRMS calcd for C10H13ClN5O3 [M+H+] 286.0701, found 286.0703.

References:

Xia, Ran;Chen, Lei-Shan [Nucleosides, nucleotides and nucleic acids,2015,vol. 34,# 10,p. 729 - 735]

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