Water → HCID 178509011, compound

HRID 500343Notes

Reaction equation

HRID 500343 reaction equation
[C@@H:1]1([N:9]2[CH:16]=[N:15][C:13]([NH2:14])=[N:12][C:10]2=[O:11])[O:8][C@H:5]([CH2:6][OH:7])[C@@H:3]([OH:4])[CH2:2]1.[BH4-].[Na+].O>C(O)C>[C@@H:1]1([N:9]2[CH2:16][NH:15][C:13]([NH2:14])=[N:12][C:10]2=[O:11])[O:8][C@H:5]([CH2:6][OH:7])[C@@H:3]([OH:4])[CH2:2]1

Participants

5

Reactant 3

HCID 962WaterHCID 4516685-Aza-2'-deoxycytidineHCID 4311764Sodium borohydride

Product 1

HCID 178509011HCID 178509011, compoundYield 86.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Method A (Reduction of 2). To a suspension of 2′-deoxy-5-azacytidine (2) (0.045 g, 0.2 mmol) in 96% ethanol (2.9 mL) was added NaBH4 (40 mg, 1.06 mmol), and the mixture was stirred for 10 min at RT. Water (4 mL) was added to the mixture giving a clear solution that was directly used for RP HPLC purification using a gradient of MeCN in 0.1 M triethylammonium bicarbonate buffer. The main fraction after evaporation provided 0.04 g of 9 as a solid. MS ES+231 [M+H+].

Workup

  1. customgiving a clear solution that
  2. customwas directly used for RP HPLC purification
  3. customThe main fraction after evaporation

Sources & evidence

ORD record
ord-5e6a03b2cdba416eab3c35b8debde49d
Source dataset
uspto-grants-2010_08
Patent number
US07772197B2

Reaction notes

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