6-(6-chloropyridin-3-yl)-1,3-dipropyl-1H-pyrrolo[3,2-d]pyrimidine-2,4(3H,5H)-dione → 6-(6-(2-(dimethylamino)ethylamino)pyridin-3-yl)-1,3-dipropyl-1H-pyrrolo[3,2-d]pyrimidine-2,4(3H,5H)-dione

HRID 2377728Notes

Reaction equation

Cl[C:2]1[N:7]=[CH:6][C:5]([C:8]2[NH:16][C:15]3[C:14](=[O:17])[N:13]([CH2:18][CH2:19][CH3:20])[C:12](=[O:21])[N:11]([CH2:22][CH2:23][CH3:24])[C:10]=3[CH:9]=2)=[CH:4][CH:3]=1>CN(C)CCN.CCO>[CH3:12][N:11]([CH3:22])[CH2:10][CH2:15][NH:16][C:2]1[N:7]=[CH:6][C:5]([C:8]2[NH:16][C:15]3[C:14](=[O:17])[N:13]([CH2:18][CH2:19][CH3:20])[C:12](=[O:21])[N:11]([CH2:22][CH2:23][CH3:24])[C:10]=3[CH:9]=2)=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 167.5 °C

Procedure

8a (135 mg) was suspended in N,N-dimethylethylenediamine (1.5 g) in EtOH (4 ml) in quartz tube and stirred at 160-175° C. under microwave (400 w) (CEM Mars) for 2 hrs. After cooling to room temperature, the solvent was removed and the solid was purified by column (26 g silica gel, RT Scientific) (CH2Cl2: MeOH=100:0 to 90:10). The fractions was evaporated and washed with ether to give the product (9c) (90 mg). HPLC condition: MeOH 40%-95% gradient in 10 minutes then MeOH 95%. Retention Time=5.32 min. 1H NMR (DMSO, d6): 0.83-0.93 (m, 6H), 1.53-1.71 (m, 4H), 2.21 (s, 6H), 2.45 (t, 2H, J=6.6 Hz), 3.38 (m, 2H), 3.85 (m, 4H), 6.55 (m, 2H), 6.73 (t, 1H, J=5.4 Hz), 7.86 (dd, 1H, J1=8.7 Hz, J2=2.4 Hz), 8.54 (d, 1H, J=2.4 Hz), 12.22 (s, 1H). MS: m/z 399 (M+H)+.

Workup

temperatureAfter cooling to room temperature
customthe solvent was removed
customthe solid was purified by column (26 g silica gel, RT Scientific) (CH2Cl2: MeOH=100:0 to 90:10)
customThe fractions was evaporated
washwashed with ether

Sources & evidence

ORD record: ord-8a997dbd18fb47b3af68625554ad49db
Source dataset: uspto-grants-2008_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07470697B2

Reaction notes

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