Chlorosuccinimide → 3-Butyl-8-chloro-1-ethyl-3,7-dihydro-1H-purine-2,6-dione

HRID 2386650

Reaction equation

[CH2:1]([N:5]1[C:13]2[N:12]=[CH:11][NH:10][C:9]=2[C:8](=[O:14])[N:7]([CH2:15][CH3:16])[C:6]1=[O:17])[CH2:2][CH2:3][CH3:4].C1C(=O)N([Cl:25])C(=O)C1>CC#N>[CH2:1]([N:5]1[C:13]2[N:12]=[C:11]([Cl:25])[NH:10][C:9]=2[C:8](=[O:14])[N:7]([CH2:15][CH3:16])[C:6]1=[O:17])[CH2:2][CH2:3][CH3:4]

Participants

Conditions

Temperature: 120 °C

Procedure

3-Butyl-1-ethyl-3,7-dihydro-1H-purine-2,6-dione (100 mg, 0.42 mmol) and NCS (56 mg, 0.42 mmol) were suspended in MeCN (5 mL) and heated at 120° C. under microwave irradiation. The reaction mixture was concentrated under reduced pressure and the title compound isolated using HPLC. [HPLC conditions used for the purification: 23 minute run time. Solvents: 0.1% TFA in MeCN and 0.1% TFA in water. MeCN increased from 5% to 95% linearly over 15 minutes. Held at 95% for 2 min. Then decreased to 5% linearly over 1 min., equilibrated at 5% for 5 minutes before next injection.]; 1H NMR (400 MHz; CDCl3) δ: 0.97 (3H, t), 1.31 (3H, t), 1.38-1.45 (2H, m), 1.72-1.80 (2H, m), 4.09-4.20 (4H, m), 13.40 (1H, br.s); m/z 271 [MH+].

Workup

concentrationThe reaction mixture was concentrated under reduced pressure

Sources & evidence

ORD record: ord-2f6cb430ddc1437faa795f9ca9917375
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08268839B2

Linked notes

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