Methanol → HCID 53697575, compound

HRID 637665Notes

Reaction equation

HRID 637665 reaction equation
[F:1][C:2]1[C:3]([NH2:18])=[N:4][C:5](=[O:17])[N:6]([CH:16]=1)[C@@H:7]1[O:15][C@H:12]([CH2:13][OH:14])[C@@H:10]([OH:11])[C@H:8]1[OH:9].[NH2:19][C:20]1[N:25]=[CH:24][CH:23]=[CH:22][N:21]=1.I([O-])(=O)(=O)=O.[Na+].CO>O>[OH:9][CH:8]1[C@H:7]([N:6]2[CH:16]=[C:2]([F:1])[C:3]([NH2:18])=[N:4][C:5]2=[O:17])[O:15][C@H:12]([CH2:13][OH:14])[CH:10]([OH:11])[N:19]1[C:20]1[N:25]=[CH:24][CH:23]=[CH:22][N:21]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 79782-AminopyrimidineHCID 168615-FluorocytidineHCID 23667635Sodium periodate

Product 1

HCID 53697575HCID 53697575, compoundYield 70.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 5-fluorocytidine (2.42 g) and 2-aminopyrimidine (0.95 g) in water (50 ml) was added sodium metaperiodate (2.13 g) under cooling with an ice-water bath. The solution was stirred at ambient temperature for 8 hours. To the reaction mixture was added methanol (50 ml). The precipitate was filtered off and the filtrate was evaporated in vacuo. The residue was triturated with acetone and air-dried to give 1-[(2R, 6R)-3,5-dihydroxy-6-hydroxymethyl-4-(2-pyrimidinyl)morpholin-2-yl]-5-fluorocytosine (2.3 g).

Workup

  1. temperatureunder cooling with an ice-water bath
  2. filtrationThe precipitate was filtered off
  3. customthe filtrate was evaporated in vacuo
  4. customThe residue was triturated with acetone
  5. customair-dried

Sources & evidence

ORD record
ord-d5654c4a56db4b3eb34ae3d0beaf4ca0
Source dataset
uspto-grants-1985_12
Patent number
US04558047

Reaction notes

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