Adenine → HCID 19027594, compound

HRID 864998Notes

Reaction equation

HRID 864998 reaction equation
[N:1]1[C:9]([NH2:10])=[C:8]2[C:4]([N:5]=[CH:6][NH:7]2)=[N:3][CH:2]=1.[C:11]([O:20][CH3:21])(=[O:19])[C:12]([CH2:14][C:15]([O:17][CH3:18])=[O:16])=[CH2:13].[H-].[Na+]>CN(C)C=O>[N:1]1[C:9]([NH2:10])=[C:8]2[C:4]([N:5]([CH2:13][CH:12]([CH2:14][C:15]([O:17][CH3:18])=[O:16])[C:11]([O:20][CH3:21])=[O:19])[CH:6]=[N:7]2)=[N:3][CH:2]=1

Participants

5

Reactant 3

HCID 190AdenineHCID 24758Sodium hydrideHCID 69240Dimethyl itaconate

Product 1

HCID 19027594HCID 19027594, compoundYield 76.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of adenine (5.40 g, 0.040 mol), dimethyl itaconate (8.00 g, 0.051 mol), sodium hydride (55% in oil, 0.2 g) and dry N,N-dimethylformamide (125 ml) was warmed to 120° C. and then kept with stirring at room temperature for 8 days. The precipitate was filtered, washed with dichloromethane (3×15 ml) and dried in vacuum to yield 8.96 g (76 g) of dimethyl 2-(adenin-9-ylmethyl)-succinate.

Workup

  1. filtrationThe precipitate was filtered
  2. washwashed with dichloromethane (3×15 ml)
  3. customdried in vacuum

Sources & evidence

ORD record
ord-55973e9ee7a5444882c53135b01fd4fc
Source dataset
uspto-grants-1996_10
Patent number
US05565461

Reaction notes

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