Potassium Carbonate → 1,3-Dibutyl-7-methanesulfonyl-3,7-dihydro-purine-2,6-dione

HRID 324979

Reaction equation

[CH2:1]([N:5]1[C:13](=[O:14])[C:12]2[NH:11][CH:10]=[N:9][C:8]=2[N:7]([CH2:15][CH2:16][CH2:17][CH3:18])[C:6]1=[O:19])[CH2:2][CH2:3][CH3:4].C(=O)([O-])[O-].[K+].[K+].[CH3:26][S:27](Cl)(=[O:29])=[O:28]>CC(C)=O>[CH2:1]([N:5]1[C:13](=[O:14])[C:12]2[N:11]([S:27]([CH3:26])(=[O:29])=[O:28])[CH:10]=[N:9][C:8]=2[N:7]([CH2:15][CH2:16][CH2:17][CH3:18])[C:6]1=[O:19])[CH2:2][CH2:3][CH3:4]

Participants

Conditions

Temperature: 23 °C

Procedure

To 500 mg (1.89 mmol) of 1,3-dibutyl-3,7-dihydro-purine-2,6-dione in 30 mL of acetone at 23° C. was added 1.04 g (7.56 mmol) of potassium carbonate followed by 0.15 mL (216 mg, 1.89 mmol) of methanesulfonyl chloride. After stirring at 23° C. for 30 min, the reaction mixture was filtered, the filtrate collected and evaporated to give a white solid. This solid was then triturated with 30 mL of petroleum ether to give 500 mg (1.46 mmol, a 77% yield) of the title compound as a white crystalline solid. mp: 98-100° C.; 1H NMR (300 MHz, CDCl3); δ 0.93-0.99 (m, 6H), 1.42-1.49 (m, 4H), 1.55-1.58 (m, 2H), 1.60-1.70 (m, 2H), 3.85 (s, 3H), 3.99-4.04 (m, 2H), ), 4.05-4.16 (t, 2H), 8.17 (s, 1H), 8.55; IR (KBr, cm−1): 3144w, 2965m, 2938m, 2876w, 1715s, 1663s, 1537s, 1442m, 1397s, 1182s, 1131,m, 761m, 670m; MS (ES) m/z (relative intensity): 343 (M++H, 100).

Workup

filtrationthe reaction mixture was filtered
customthe filtrate collected
customevaporated
customto give a white solid
customThis solid was then triturated with 30 mL of petroleum ether
customto give 500 mg (1.46 mmol

Sources & evidence

ORD record: ord-b6e6973d395f470fa1a32220cbe95661
Source dataset: uspto-grants-2001_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06221874B1

Linked notes

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