Diethyl Ether → 2,5-Methano-5H,9H-pyrimido(2,1-b)(1,5,3)dioxazepin-9-one, 2,3-dihydro-3-(hydroxymethyl)-8-methyl-, (2R,3R,5R)-

HRID 2072852

Reaction equation

HRID 2072852 reaction equation
[CH3:1][C:2]1[C:8](=[O:9])[NH:7][C:5](=O)[N:4]([C@@H:10]2[O:14][C@H:13]([CH2:15][OH:16])[C@@H:12]([OH:17])[C@H:11]2O)[CH:3]=1.C(=O)(OC1C=CC=CC=1)OC1C=CC=CC=1.C(OCC)C>CN(C=O)C.CO.C(=O)(O)[O-].[Na+]>[CH3:1][C:2]1[C:8](=[O:9])[N:7]=[C:5]2[N:4]([C@@H:10]3[O:14][C@H:13]([CH2:15][OH:16])[C@H:12]([O:17]2)[CH2:11]3)[CH:3]=1

Participants

7

Reactant 3

HCID 3283Diethyl EtherHCID 7597Diphenyl carbonateHCID 4454085-Methyluridine

Product 1

HCID 4579822,5-Methano-5H,9H-pyrimido(2,1-b)(1,5,3)dioxazepin-9-one, 2,3-dihydro-3-(hydroxymethyl)-8-methyl-, (2R,3R,5R)-Yield 101.4%

Reagents, catalysts & solvents 3

HCID 516892Sodium BicarbonateCatalystHCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
150 °C

Procedure

A 100 mL round bottom flask equipped with magnetic stir bar, reflux condensor, and nitrogen inlet was charged with 5 g of ribothymidine, 4.7 g (1.2 eq) of diphenyl carbonate and 150 mg of sodium bicarbonate in 10 mL of DMF. The mixture was heated to 150° C. for 35 minutes. The black solution was diluted with 10 mL of MeOH and slowly added to 200 mL of diethyl ether. The tan product was filtered and dried to yield 4.4 g (96%) of anhydrothymidine.

Workup

  1. customA 100 mL round bottom flask equipped with magnetic stir bar
  2. temperaturereflux condensor, and nitrogen inlet
  3. filtrationThe tan product was filtered
  4. customdried

Sources & evidence

ORD record
ord-c0b3691bde8f4128a9160c5ebc5206ac
Source dataset
uspto-grants-1990_04
Patent number
US04914233

Linked notes

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