Adenine → 6-Benzamidopurine

HRID 535258Notes

Reaction equation

HRID 535258 reaction equation
[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N:10]1[C:18]([NH2:19])=[C:17]2[C:13]([N:14]=[CH:15][NH:16]2)=[N:12][CH:11]=1>N1C=CC=CC=1>[C:1]([NH:19][C:18]1[N:10]=[CH:11][N:12]=[C:13]2[C:17]=1[NH:16][CH:15]=[N:14]2)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 190AdenineHCID 7412Benzoyl chloride

Product 1

HCID 970756-Benzamidopurine

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Benzoyl chloride (1.3 mL, 11 mmol) was added dropwise over 30 min to a stirred suspension of adenine (1.35 g, 10 mmol) in dry pyridine, and stirring was continued at 100° C. for a further 3 h, and the reaction mixture was allowed to stand overnight at room temperature. The reaction was quenched with methanol and the solvents were removed under reduced pressure. The residue was triturated in hot isopropanol and dried in vacuo to give 8 as a white solid: yield 2.15 g (90%); MS (+ESI): m/z 240 [M+H]+; 1H NMR (400 MHz, d-DMSO): δ11.50 (s, 1H), 8.74 (s, 1H), 8.52 (s, 1H), 8.11 (d, 2H, J=7.2 Hz), 7.66 (t, 1H, J=7.2 Hz), 7.58 (t, 2H, J=7.2 Hz).

Workup

  1. waitto stand overnight at room temperature
  2. customThe reaction was quenched with methanol
  3. customthe solvents were removed under reduced pressure
  4. customThe residue was triturated in hot isopropanol
  5. customdried in vacuo

Sources & evidence

ORD record
ord-e99a593aae7743fba68fb29a998216c9
Source dataset
uspto-grants-2014_10
Patent number
US08859490B2

Reaction notes

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