Adenine → HCID 128982, compound

HRID 1789326Notes

Reaction equation

HRID 1789326 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.[O-:11][CH2:12][CH3:13].[Na+].[Cl-].[NH4+].[CH3:17]N(C)C=O>C(O)C>[N:1]1[C:9]([NH2:10])=[C:8]2[C:4]([N:5]([CH:17]=[CH:13][CH:12]=[O:11])[CH:6]=[N:7]2)=[N:3][CH:2]=1

Participants

6

Reactant 4

HCID 190AdenineHCID 6228DimethylformamideHCID 25517Ammonium ChlorideHCID 2723922Sodium ethoxide

Product 1

HCID 128982HCID 128982, compoundYield 52.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of adenine (135 mg; 1 mmole) in dimethylformamide (2 ml) at -40° there is added a solution of sodium ethoxide (prepared from 15 mg of sodium hydride) in ethanol (1 ml) and the mixture is stirred for 10 min. Propargyl aldehyde (59 mg; 1.1 mmole) is added in one portion and stirring is continued at -40° for 1 hr. The pale brown reaction mixture is then allowed to come to room temperature and neutralized by the addition of aqueous ammonium chloride. The precipitated solid (100 mg) is removed by filtration. It is recrystallized by dissolution in boiling water (240 ml) followed by cooling. This affords to the pure title compound (100 mg., 52.9%) m.p. 258°-60° C. The NMR spectrum of the material is in agreement with the postulated structure and shows absorption peaks at (DMSO) 7.17 (q,J,=7.8 HzJ2 =14.4 Hz, 1H, --CH=CH--CHO) 7.55 (S, 2H, NH2) 8.28 (S, 1H) 8.54 (d, J, J=14.4 Hz, 1H CH=CH--CHO) 8.64 (S, 1H) 9.68 (d, J-7.9 Hz, CHO). Mass spectrum m/z (intensity, % of base peak), ion: 189 (55.7)M+, 161 (98) (M-CO)+, 160 (32) (M-HCO)+, 134 (100) (MC3H∂)M+, 161 (98) (M-CO)+, 160 (32) (M-HCO)+, 134 (100) (MC3H3O)+, 118 (93).

Workup

  1. stirringstirring
  2. waitis continued at -40° for 1 hr
  3. customto come to room temperature
  4. customThe precipitated solid (100 mg) is removed by filtration
  5. customIt is recrystallized by dissolution
  6. temperatureby cooling

Sources & evidence

ORD record
ord-641689d78f1e402c9f9195a831d149ca
Source dataset
uspto-grants-1987_08
Patent number
US04689321

Reaction notes

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