Azacytidine → HCID 14329828, compound

HRID 2232209Notes

Reaction equation

HRID 2232209 reaction equation
[C@@H:1]1([N:10]2[CH:17]=[N:16][C:14]([NH2:15])=[N:13][C:11]2=[O:12])[O:9][C@H:6]([CH2:7][OH:8])[C@@H:4]([OH:5])[C@H:2]1[OH:3].[CH3:18][O:19][C:20]1[CH:41]=[CH:40][C:23]([C:24](Cl)([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[C:25]2[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=2)=[CH:22][CH:21]=1>N1C=CC=CC=1>[CH3:32][O:31][C:28]1[CH:27]=[CH:26][C:25]([C:24]([O:8][CH2:7][C@H:6]2[O:9][C@@H:1]([N:10]3[CH:17]=[N:16][C:14]([NH2:15])=[N:13][C:11]3=[O:12])[C@H:2]([OH:3])[C@@H:4]2[OH:5])([C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=2)[C:23]2[CH:40]=[CH:41][C:20]([O:19][CH3:18])=[CH:21][CH:22]=2)=[CH:30][CH:29]=1

Participants

4

Reactant 2

HCID 9444AzacytidineHCID 968311,1'-(Chlorophenylmethylene)bis(4-methoxybenzene)

Product 1

HCID 14329828HCID 14329828, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 5-azacytidine (2.20 g, 9 mmol) in dry pyridine (45 mL) was added 4,4'-dimethoxytrityl chloride (3.15 g, 9.3 mmol) and the mixture was stirred overnight. The reaction mixture was poured into ice-water and extracted with chloroform. The combined organic extracts were dried (MgSO4) and chromatographed through a silica gel column (ethyl acetate--10% methanol/ethyl acetate) to give 2.89 g (59%) of a white product. NMR (CDCl3 +D2O); δ 3.35 (m, 2H), 3.70 (s, 6H), 4.26 (m, 3H), 5.80 (d, 1H), 6.80 (m, 4H), 7.31 (m, 9H), 8.45 (s, 1H).

Workup

  1. extractionextracted with chloroform
  2. dry with materialThe combined organic extracts were dried (MgSO4)
  3. customchromatographed through a silica gel column (ethyl acetate--10% methanol/ethyl acetate)

Sources & evidence

ORD record
ord-a396ff891cee4fa3b84d07a28ce7ea32
Source dataset
uspto-grants-1988_11
Patent number
US04788181

Reaction notes

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