Ethyl bromoacetate → 9H-Purine-9-acetic acid, 6-(benzoylamino)-, ethyl ester

HRID 535259Notes

Reaction equation

[C:1]([NH:9][C:10]1[N:18]=[CH:17][N:16]=[C:15]2[C:11]=1[NH:12][CH:13]=[N:14]2)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].Br[CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24]>CN(C=O)C>[C:1]([NH:9][C:10]1[N:18]=[CH:17][N:16]=[C:15]2[C:11]=1[N:12]=[CH:13][N:14]2[CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 0 °C

Procedure

Compound 8 (2.39 g, 10 mmol) was dissolved in dry DMF (100 mL), cooled to 0° C., sodium hydride (0.48 g, 20 mmol) was added, and the mixture stirred at room temperature for 30 min. Ethyl bromoacetate (1.22 mL, 11 mmol) was added dropwise for 1 h. Stirring was continued for 2 h at room temperature and the reaction was quenched with methanol (2 mL). The solvents were evaporated under reduced pressure. The residue was subjected to column chromatography (DCM/MeOH; 9.5/0.5) to obtain 9 as a white solid: yield 1.3 g (40%); MS(+ESI): m/z 326 [M+H]+; 1H NMR (400 MHz, CDCl3): δ9.02 (s, 1H), 8.83 (s, 1H), 8.11 (s, 1H), 8.05 (d, 2H, J=7.2 Hz), 7.62 (t, 1H, J=7.2 Hz), 7.54 (t, 2H, J=7.2 Hz), 5.06 (s, 2H), 4.31 (q, 2H, J=7.2 Hz), 1.38 (t, 3H, J=7.2 Hz); 13C NMR (400 MHz, CDCl3): δ=166.76, 164.53, 152.96, 152.50, 149.83, 143.22, 133.68, 132.80, 128.89, 127.85, 122.56, 62.53, 44.33, 14.09.

Workup

stirringStirring
waitwas continued for 2 h at room temperature
customthe reaction was quenched with methanol (2 mL)
customThe solvents were evaporated under reduced pressure

Sources & evidence

ORD record: ord-62812fdd2e5b4d219818e9f6e9673a99
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08859490B2

Reaction notes

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