Trifluoromethanesulfonic acid → 5-Aza-2'-deoxycytidine

HRID 1510806Notes

Reaction equation

C(O[CH:5]1[O:19][C@H:18]([CH2:20][O:21]C(=O)C2C=CC(Cl)=CC=2)[C@@H:7]([O:8]C(=O)C2C=CC(Cl)=CC=2)[CH2:6]1)(=O)C.C[Si]([NH:35][C:36]1[N:41]=[C:40]([O:42][Si](C)(C)C)[N:39]=[CH:38][N:37]=1)(C)C.S(O)(C(F)(F)F)(=O)=O.CO[Na]>CO.CS(C)=O.CC#N>[CH2:6]1[C@H:5]([N:39]2[C:40](=[O:42])[N:41]=[C:36]([NH2:35])[N:37]=[CH:38]2)[O:19][C@H:18]([CH2:20][OH:21])[C@H:7]1[OH:8]

Participants

Conditions

Temperature: 0 °C

Procedure

A mixture of MeCN (45 mL), 1-O-acetyl-3,5-di-O-(4-chlorobenzoyl)-2-deoxy-D-ribofuranose (3.0 g), 2-[(trimethylsilyl)amino]4-[(trimethylsilyl)oxy]-s-triazine (1.78 g) and TfOH (0.5 g) were stirred at about 0° C. for 24 hours. DMSO (6 mL) was added and the mixture was evaporated at 30˜50° C. under reduced pressure to remove the MeCN. A 29% solution of MeONa in MeOH (1.8 g, 9.9 mmol, 1.5 eq.) was added with stirring at about 20˜25° C. After the reaction was complete, MeOH was added to effect precipitation and the solid was filtered, washed and dried to give crude decitabine. API grade decitabine (>99.0 HPLC purity) is prepared by the recrystallization of crude decitabine from MeOH, followed by three washes with MeOH and drying at 40° C. under vacuum.

Workup

customthe mixture was evaporated at 30˜50° C. under reduced pressure
customto remove the MeCN
stirringwith stirring at about 20˜25° C
filtrationthe solid was filtered
washwashed
customdried

Sources & evidence

ORD record: ord-cded6097e2864d85ac31614ee62d7046
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08212021B2

Reaction notes

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