Butylamine → HCID 27370798, compound

HRID 1616103Notes

Reaction equation

Br[C:2]1[N:10]([CH2:11][C:12](=[O:19])[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:9]2[C:8](=[O:20])[NH:7][C:6](=[O:21])[N:5]([CH3:22])[C:4]=2[N:3]=1.C(N(C(C)C)CC)(C)C.[CH2:32]([NH2:36])[CH2:33][CH2:34][CH3:35]>CCO>[CH2:32]([NH:36][C:2]1[N:10]([CH2:11][C:12](=[O:19])[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:9]2[C:8](=[O:20])[NH:7][C:6](=[O:21])[N:5]([CH3:22])[C:4]=2[N:3]=1)[CH2:33][CH2:34][CH3:35]

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of commercially available 8-bromo-3,7-dihydro-3-methyl-7-(2-oxo-2-phenylethyl)-1H-purine-2,6-dione (42, 50 mg, 0.138 mmol), diisopropylethylamine (47 μL, 0.275 mmol) and butylamine (27 μL, 0.275 mmol) in EtOH (1 mL) was heated at 120° C. for 12 h. The reaction was cooled to room temperature, the solid was filtered off, washed with water, affording the desired product as a white solid (22 mg, 44% yield). 1H NMR (400 MHz, DMSO-d6): δ=11.57 (s, 1H), 8.04 (d, J=7.8 Hz, 2H), 7.72 (t, J=7.8 Hz, 1H), 7.60 (t, J=7.8 Hz, 2H), 6.99 (t, J=5.5 Hz, 1H), 5.62 (s, 2H), 3.32 (s, 3H), 3.32 (m, 2H), 1.51 (quint, J=7.4 Hz, 2H), 1.31 (sext, J=7.4 Hz, 2H), 0.88 (t, J=7.4 Hz, 3H); 13C NMR (125 MHz, DMSO-d6): δ=192.2, 154.6, 153.0, 150.7, 150.0, 134.1, 133.8, 128.7, 127.9, 101.7, 49.5, 41.8, 31.0, 28.2, 19.2, 13.5; IR (film): ν=3361, 3008, 2827, 1681, 1485, 1425, 1230, 746 cm−1; HRMS (ESI): m/z: calcd for C18H21N5O3Na+: 378.1542, found: 378.1545.

Workup

temperatureThe reaction was cooled to room temperature
filtrationthe solid was filtered off
washwashed with water

Sources & evidence

ORD record: ord-1841ce94909840d98d2538e3f9daefa4
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08765775B2

Reaction notes

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