HCID 14329840, compound → 2'-3'-Dideoxy-5-azacytidine

HRID 2232210Notes

Reaction equation

HRID 2232210 reaction equation
COC1C=CC(C([O:22][CH2:23][C@H:24]2[O:28][C@@H:27]([N:29]3[CH:36]=[N:35][C:33]([NH2:34])=[N:32][C:30]3=[O:31])[CH2:26][CH2:25]2)(C2C=CC=CC=2)C2C=CC(OC)=CC=2)=CC=1>C(Cl)(Cl)Cl>[C@@H:27]1([N:29]2[CH:36]=[N:35][C:33]([NH2:34])=[N:32][C:30]2=[O:31])[O:28][C@H:24]([CH2:23][OH:22])[CH2:25][CH2:26]1

Participants

3

Reactant 1

HCID 14329840HCID 14329840, compound

Product 1

HCID 4518512'-3'-Dideoxy-5-azacytidineYield 58.9%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Compound 9 (0.08 g, 0.16 mmol) was dissolved in chloroform (2 mL) and poured onto a silica gel column (3 g, Whatman Partisil 40). The column was washed with benzene (40 mL) and left at ambient temperature for 24 h. The column was eluted with ethyl acetate followed by 10% methanol/ethyl acetate to give 0.02 g of crude product along with 0.04 g of unchanged starting material. The crude product was dissolved in water, filtered through a Millex-GS Filter, and the filtrate was chromatographed through a C18 reverse-phase column (10% methanol/water) to give 0.005 g (30%) of white, lyophilized product. NMR (D2O); δ 2.06 (m, 4H), 3.72 (m, 2H), 4.18 (m, 1H), 5.89 (d, 2H, J=5 Hz), 8.51 (s, 1H). FAB mass spectrum, m/z (relative intensity) 113 (b+2H, 100), 213 (MH+, 88). MH+ calc. 213.0988; found 213.0991±0.0020 (n=8).

Workup

  1. additionpoured onto a silica gel column (3 g, Whatman Partisil 40)
  2. washThe column was washed with benzene (40 mL)
  3. washThe column was eluted with ethyl acetate

Sources & evidence

ORD record
ord-11fbb1964a254cef9d854eeefc5b0eca
Source dataset
uspto-grants-1988_11
Patent number
US04788181

Reaction notes

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